Gusto jobs in Denver, CO

About the Role: We're hiring a Senior Staff Product Designer to define, ship, and scale a new Benefits product area. In this role, you'll design the software to service experience, with a focus on the role AI will play to connect the digital experience, support, sales and operations teams while maintaining the warmth and clarity customers expect from Gusto. You'll operate at two altitudes: set the north star vision for an emerging area, then drive an MVP and fast iterations that prove value, de‑risk, and lay the groundwork for rapid scale. You'll collaborate with Product, Engineering, and Data to design agentic workflows (what the system does), human-in-the-loop moments (what experts do), and clear decision policies for when to automate, escalate, or pause. Your work should measurably reduce customer effort, increase accuracy and compliance, and bend cost-to-serve down while keeping the experience warm and trustworthy. About the Team: Product Design at Gusto is a multidisciplinary team of designers, researchers, writers, and front-end developers creating intelligent, human-centered experiences for small businesses and their teams. We use data, empathy, and craft to make complex systems like payroll and benefits feel clear, capable, and kind. Gusto is defining what it means to be an AI-native company, and Product Design is at the center of that transformation. We're moving fast, experimenting boldly, and shaping how intelligent systems can empower our small business customers. Designers here have the autonomy to influence both how we work and what we build-accelerating our customers' progress and helping them reconnect with the missions that drive their work. If you're passionate about crafting the next era of product design and helping small businesses harness the power of AI, come join us. Here's what you'll do day-to-day: * Chart the path forward: Drive 0→1 strategy for a new product area, creating a north star that shows how humans and AI collaborate to deliver accurate, empathetic, and scalable experiences for small businesses. * Design experiences that empower: Define first principles approach to help teams decide when automation should act, when people should lead, and how systems learn over time. * Bridge software and service: Partner with CX and Operations to design a human + AI service model where AI is the connective tissue that streamlines workflows, reduces cognitive load, and prepares the system for rapid scale. * Partner to make it real: Work across Gusto to collaborate with Product, Engineering, and Data to define and execute your strategic vision. Build systems and rituals to prototype, evaluate, and safely scale AI capabilities. * Elevate the bar: Work fluently with AI as a design material. Shape design systems and evaluation patterns that raise both the craft and ethics of intelligent experience design across the company. * Measure what matters: Design for observability and feedback so every model decision can be measured, adjusted, and improved through real-world signals. Here's what we're looking for: * 10+ years of product design experience, with a proven track record of leading at the product or portfolio level, including multiple 0-to-1 launches that scaled. * Builder mindset: Hands-on craft paired with strong product sense. You've shipped ambitious ideas, influenced strategy, and driven alignment through design. * Comfort with complexity: Experience creating simple, guided experiences in domains that are regulated, multi-actor, or technically dense. * Service design fluency: Experienced in crafting end-to-end journeys where software, people, and policy work together. You see CX and Ops as co-designers, not downstream recipients. * AI as design material: You've designed AI-assisted or AI-powered experiences that simplify workflows, guide decision-making, or enhance human judgment. You understand how to shape prompts, evaluate outcomes, and design for transparency, safety, and trust. * Strategic acumen: Ability to contribute directly to business and product strategy, influence executive stakeholders, and connect design outcomes to measurable impact. * High quality bar: Advocate for design craft and accessibility while delivering iteratively; you balance speed with raising the bar. * Collaborative leadership: Known for mentoring senior ICs, shaping org-wide opinions, and creating leverage across teams. * Passion for Gusto's mission: Deep empathy for small businesses and a belief in the power of benefits to transform lives. At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto's compensation philosophy and benefits offerings please view our Total Rewards Approach page. Our cash compensation range for this role is $172,000/yr to $215,000/yr in Denver & most remote locations, and $202,000/yr to $253,000/yr in San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Team: This team powers the technology, data, and processes that enable Gusto's go-to-market (GTM) organization to operate with clarity, efficiency, and scale. We build and manage the Salesforce ecosystem and connected GTM tools that drive how Sales and Marketing engage with prospects and customers. Our mission is to create a seamless, data-driven foundation for growth - ensuring every GTM team has the insights, automation, and systems they need to deliver exceptional customer experiences and drive predictable revenue. The team partners closely with Sales, Revenue Operations, and Growth leadership to translate strategy into scalable systems that improve pipeline visibility, forecasting accuracy, and sales productivity. As part of the broader Growth organization, we sit at the intersection of technology and business strategy - responsible for architecting and evolving the platforms that fuel Gusto's revenue engine. With growing investment in AI and automation, the team plays a critical role in shaping how Gusto uses intelligent systems to identify ideal customers, personalize engagement, and accelerate growth. Here's what you'll do day-to-day: Own and Evolve: Lead the strategy, architecture, and evolution of Gusto's GTM business systems - including Salesforce and connected tools - to power how our Sales and Marketing teams engage customers, manage pipeline, and drive revenue growth. Define the Vision: Establish and execute a multi-year roadmap for GTM systems that aligns with company growth priorities - ensuring scalability, data integrity, and cross-functional alignment across Growth, RevOps, and Engineering. Partner Cross-Functionally: Collaborate closely with Sales, Revenue Operations, Growth, and Finance leaders to translate business needs into scalable systems and process solutions that improve forecasting accuracy, sales productivity, and customer experience. Leverage AI and Automation: Integrate AI-driven capabilities into GTM systems - such as lead scoring, forecasting, prioritization, and personalized engagement - to accelerate decision-making and drive smarter, data-informed growth. Lead and Develop: Manage and mentor a team of Business Systems Analysts, fostering a culture of technical excellence, collaboration, and continuous improvement. Drive Adoption and Change: Champion new tools and processes across GTM teams, ensuring seamless adoption, strong communication, and measurable business impact. Here's what we're looking for: 10+ years of experience leading GTM Business Systems teams in a high-growth environment, with deep expertise in Salesforce architecture, configuration, and administration. Proven track record of designing, integrating, and scaling Salesforce and related GTM platforms to enable efficient sales execution and predictable revenue growth. Hands-on technical fluency - comfortable diving into system configuration, automation, and data modeling to diagnose and solve complex problems directly. Experience leading and developing Business Systems Analysts and cross-functional project teams, fostering a culture of technical excellence, business alignment, and operational rigor. Strong partnership orientation, with demonstrated success collaborating closely with Sales, RevOps, Growth, and Finance to translate strategy into scalable systems and processes. Strategic thinker and systems architect, able to balance quick delivery with long-term design principles, aligning technology investments with GTM and company growth objectives. Proven ability to leverage AI and automation within GTM systems to identify ideal customers, prioritize opportunities, and personalize engagement. Change leader and communicator, adept at driving adoption across Sales and GTM teams, managing stakeholders, and influencing executives through clarity, trust, and results. Our cash compensation amount for this role is targeted at $155,000 to $194,000/yr in Denver, $184,000 to $229,000/yr for San Francisco, New York, & Seattle. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: Gusto is seeking an experienced ontologist and taxonomist who will be a key collaborator in building next-generation, AI-powered knowledge systems, enhancing how knowledge is created, delivered, and experienced by our customers and internal teams (Gusties). You will design, implement, and maintain the semantic structures that train, guide, and give context to AI tools, ensuring our content is accurate and personalized. Your work will accelerate our mission to ensure each Gustie is AI native through key initiatives that scale the business. About the Team: This role is a strategic partner for leadership across Content, CX, Product Management, Engineering, and Data Science. You will be responsible for identifying, planning, and executing a roadmap that leverages AI for content automation and intelligent service delivery inclusive of creating AI agents to amplify efficiency, scale, and impact. You will collaborate with cross-functional teams to ensure our taxonomies and ontologies are the foundation of our AI content strategy, enabling enhanced data interoperability, automated content workflows, and sophisticated knowledge discovery. Here's what you'll do day-to-day: Lead Gusto's efforts in building an enterprise taxonomy and ontology management platform from RFP to implementation, focusing specifically on enablement for knowledge graph capabilities and integration with related semantic systems (Schema App, Neo4j, Cube, etc.) Design, develop, and maintain scalable taxonomies and ontologies that serve as the backbone for AI content generation, personalization, and retrieval systems. Create and implement intuitive taxonomy structures to train and fine-tune AI models, ensuring accurate, context-aware, and on-brand content delivery. Partner with Product, Engineering, Data Science, and Content teams to design and automate content workflows, integrating semantic models to power generative AI, content strategy, and intelligent automation. Establish governance frameworks for taxonomy, ontology, and AI-generated semantic data, providing guidance, training, and quality assurance to internal stakeholders. Analyze content performance and user interaction data to continuously refine and improve AI model outputs and semantic structures. Stay abreast of emerging trends in AI, particularly generative AI, large language models (LLMs), and semantic technologies, and incorporate cutting-edge methods to enhance Gusto's knowledge infrastructure. Here's what we're looking for: 8+ years of experience in taxonomy development and/or ontology design, with demonstrated experience applying these skills to AI-driven systems. Deep understanding of AI and machine learning principles, especially in relation to Natural Language Processing (NLP), generative AI, and Large Language Models (LLMs). Experience using AI/ML principles to inform taxonomy and ontology development and governance. Hands-on experience with AI content creation, prompt engineering, and workflow automation tools (e.g., generative AI platforms, content management systems with AI integration). Proven ability to develop and implement content strategies that leverage AI for personalization, delivery, and optimization. Practical knowledge of customer support processes and the ability to translate business needs into scalable semantic data solutions. Experience with Semantic Web technologies (RDF, OWL, SKOS), query languages (SPARQL), and ontology editing tools, with a clear understanding of how they power AI reasoning and knowledge graphs. Strong problem-solving capabilities, attention to detail, and the ability to work effectively across departments, balancing technical precision with practical application. Outstanding communication and storytelling skills for translating complex technical work into actionable insights for diverse stakeholders. Proficiency in data analysis and a strong understanding of user experience principles. Our cash compensation amount for this role is $157,000/yearly to $187,000/yearly in Denver & most major metro locations, and $185,000/yearly to $220,000/yearly for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: We're expanding our Sales team and looking for driven Business Development Representatives (BDRs) to generate new opportunities. This role is for someone who gets energy from outbound prospecting, sparking interest in innovative technology, and initiating strategic conversations. As a BDR, you'll play a crucial role at the top of our sales funnel - identifying high-potential clients, qualifying interest, and booking meetings. You'll partner closely with Account Executives and collaborate cross-functionally to turn curiosity into action. Here's what you'll do day-to-day: Outbound Prospecting: Conduct over 100 cold calls to prospective buyers, facilitating next steps such as scheduling meetings for account executives to further qualify leads. Qualify Opportunities: Identify and nurture a large volume of prospects to qualify leads through multiple channels. Educate & Inspire: Communicate Gusto Pro's value to prospects, highlighting how our platform helps firms streamline operations and better serve their clients. Collaborate with AEs: Partner with Account Executives to drive pipeline generation, account planning, and meeting conversion. Maintain CRM Hygiene: Accurately log all activities and insights in Salesforce and maintain a disciplined, data-driven approach to outreach. Hit Goals & Grow: Consistently meet monthly metrics and contribute to a high-performing team culture focused on results and career development. Here's what we're looking for: 1+ years of B2B sales or outbound prospecting experience, ideally in SaaS, HCM, HR Tech, or FinTech. Expertise in outbound prospecting and sales strategy, with a proven track record of success. Advanced written and verbal communication skills, with the ability to craft and deliver compelling messaging. Strong command of Salesforce, Outreach, LinkedIn Sales Navigator, and similar tools with demonstrated mastery in managing the sales pipeline. Strong judgment in handling complex situations, including decision-making in ambiguous or challenging scenarios. Able to mentor junior team members and provide guidance on best practices and strategy. Takes initiative and requires minimal direction, with the ability to work independently and collaboratively with cross-functional teams. Ability to engage with high-level decision-makers and executives. Our cash compensation range for this role ranges from $27.17 - $31.90 per hour with a 20% commission structure in the Denver location. Final offer amounts are determined by multiple factors, including candidate location, experience, and expertise, and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: As the Head of Revenue Analytics at Gusto, you will lead a critical function responsible for using data to measure, analyze, and optimize the drivers of our Go-to-Market revenue. Reporting to the Head of Revenue Operations, you will be a strategic partner to our GTM and Product teams, using a deep understanding of customer behavior and market trends to drive growth, retention, and profitability. You will lead a team of Gusties responsible for revenue forecasting, marketing analytics, and customer expansion insights, working cross-functionally with Sales, Marketing, Finance, Data, and Product to guide Gusto's growth strategy. The ideal candidate is an exceptional data leader who can balance strategic vision with hands-on analytical work - someone equally comfortable shaping forecasts at the executive level and rolling up their sleeves to build reports or run ad-hoc analyses when needed. What You'll Do: Strategic Leadership: Develop and execute a comprehensive revenue analytics strategy that aligns with GTM's overall business goals. Partner with GTM and R&D leaders to provide the data and insights needed to make informed, data-driven decisions. Forecasting & Planning: Lead the design and execution of revenue forecasts across acquisition, expansion, and retention. Provide Finance and GTM leaders with accurate, transparent, and actionable views of performance. Marketing Analytics: Drive analysis of acquisition efficiency, ROI, attribution, and customer lifecycle value to optimize spend and guide strategic bets. Customer & Retention Insights: Deliver churn, retention, and CLV analysis to inform strategies for engagement, upsell, and long-term profitability. Insights and Recommendations: Conduct deep-dive analyses to identify revenue drivers and anomalies. Translate complex data into clear, actionable insights and recommendations for senior leadership and cross-functional partners. Quota & Budget Alignment: Partner with Finance and GTM leaders to support quota setting, budget allocation, and performance tracking. Data Products & Infrastructure: Build and scale datasets, dashboards, and tools that provide self-serve access to revenue insights while ensuring data quality and consistency. AI-Driven Analytics: Evaluate and apply AI/ML techniques to enhance forecasting, attribution, and customer lifecycle modeling. Stay ahead of emerging AI tools that can drive efficiency and accuracy in revenue analytics. Cross-Functional Collaboration: Serve as a critical partner to Sales Ops, GTM Analytics, Marketing Ops, and Finance in aligning data and insights across the funnel. People Empowerment: Recruit, mentor, and develop a high-performing analytics team. Foster a culture of curiosity, analytical rigor, and operational excellence to deliver impact across the business. What We're Looking For: 12+ years of experience in analytics, forecasting, or revenue strategy, with at least 5+ years in a leadership role. Leadership with a Builder Mindset: A dynamic leader who inspires and develops teams while maintaining a “roll up your sleeves” attitude - able to step into the details when needed to build reports, run analyses, and troubleshoot. Analytical Expertise: Strong analytical skills with expertise in data analysis and visualization tools (e.g., SQL, Tableau, Power BI). Experience with financial and marketing forecasting models. SaaS/Growth Background: Proven track record of successfully building and leading analytics functions in a high-growth SaaS or technology environment. Technical Skills: Familiarity with various data sources and technologies, including Salesforce, marketing automation platforms, and data warehouses. AI Fluency: Awareness of how AI/ML is transforming analytics, with the ability to partner with data science and engineering teams to pilot and operationalize AI-driven approaches. Skilled at discerning when AI adds value and when traditional methods are more appropriate. Business Acumen: Deep understanding of the entire customer lifecycle, from acquisition to retention, and how each stage impacts revenue. Communication & Influence: Excellent communication and presentation skills with the ability to distill complex data into clear, actionable insights for both technical and non-technical audiences. Compensation Our annual base salary compensation range for this role is $201,200 - $251,500 in San Francisco & New York, and $171,200 - $214,000 in Denver. This role is also eligible for an annual variable cash bonus (up to 20%). Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

About the Role: Are you a tax expert with a passion for technology and innovation? Join our Tax Credits team and help shape the future of tax credit software. As the Head of Tax Credits Compliance, you will play a crucial role in ensuring our product remains accurate, compliant, and easy to use. Your expertise will be instrumental in developing new features, supporting clients with their compliance-related requests, and helping our app stay ahead of industry trends. This role requires working across multiple teams to help democratize tax credits for small businesses by streamlining tax credit filings. This is an exciting opportunity to join a dynamic team and make a real impact on small businesses all across America. About the Team: The Tax Credits team is on a mission to democratize tax credits. We aim to make access to tax credits ubiquitous for SMBs & business advisors, ensuring every business receives the financial support they deserve to fuel growth, innovation and long-term success. Here's what you'll do day-to-day: * Tax Research: Conduct in-depth research on tax credits, including R&D tax credits, 401K, FICA Tips, WOTC, and other relevant incentives, to identify new opportunities and stay ahead of industry trends. Assist Gusto with bringing new credits to its client base. * Product Development: Collaborate closely with our engineering and product teams to develop and enhance our tax credit software, ensuring it remains compliant with the latest tax laws and regulations. Help identify ways to educate and assist small businesses with tax credit filings. * Compliance: Collaborate with our central Legal & Compliance team and Ops teams to ensure our service remains compliant and provide guidance to teams on compliance matters. * Client Support: Serve as the go-to expert for client escalations related to tax credits, providing timely and accurate responses. Here's what we're looking for: * Experience: 10+ years in tax compliance, preferably with a focus on federal and state tax credits * Product Development: experience working at a software company and/or in a product-oriented environment, with a demonstrated ability to translate technical tax concepts into innovative product features * Communication: Excellent communication skills, both written and verbal, to effectively interact with clients, team members, and stakeholders. * Problem-Solving: A strong problem-solving mindset, with the ability to identify and resolve complex tax issues and find innovative solutions to multi-stakeholder questions. * Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving. * Leadership: Strong leadership skills, with the ability to inspire and motivate cross-functional teammates to achieve remarkable results. * Education: * Bachelor's degree in accounting, finance, or a related field. * Master's degree in taxation or a similar field is preferred but not required * Certifications: * Juris Doctor (JD) or Certified Public Accountant (CPA) is required (active or inactive) * Chartered Tax Practitioner (CTP) or IRS Enrolled Agent (EA), any additional certifications related to tax credits, such as the R&D Credit Certification, are a plus Our cash compensation amount for this role is $155,745 to $183,000/yr in Denver, $175,510 to $215,000/yr for San Francisco, Seattle & New York, and $169,360 to $199,000/yr for Los Angeles. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role: Gusto is looking for highly skilled and motivated Data Scientists with extensive experience (10+ years) applying their expertise in a business environment. As a Principal Data Scientist, you will play a crucial role in leveraging experimentation, statistical inference, and causal analysis to drive strategic decision making that contributes to the overall success of our organization. The ideal candidate is a trusted data storyteller with strong statistical and coding skills, and a passion for applying these skills to help small businesses thrive. In this role you will work closely with our Product, Engineering, Design, Finance, and other Data teams to become an expert in the data for your domain, define and track metrics that help us understand our business performance, and dive deep into our Payroll, Benefits, and HR data to deliver insights and answer questions. You'll also integrate AI-assisted practices to accelerate analysis, enhance rigor, and expand the reach of insights across Gusto. We have multiple senior roles open, each focused on a different area of our business Here's what you'll do day-to-day: * Strategic Leadership: Shape the analytical strategy for a major product or business area. Identify high-leverage opportunities, set long-term measurement and experimentation direction, and align executive stakeholders around data-driven priorities. * Execution Excellence: Drive and execute on org-level analytical roadmaps that shape company strategy. Achieve alignment and ensure consistent analytical rigor and metric integrity across product domains. * Scaled Impact: In addition to being an expert in statistical methods and driving impact through execution, you will drive frameworks for experimentation, causal analysis, and metric design that scale across multiple teams and influence org-wide decision quality. * Thought Partnership: Serve as a trusted advisor to senior product, engineering, and business leaders. Anticipate emerging questions, proactively define success measures, and advocate for data-informed strategy across the org. * Analytical Innovation: Push the boundaries of statistical modeling, experimentation, and AI-assisted analytics. Design methods and tools that expand how Gusto leverages data to drive customer and business impact. * Mentorship: Mentor and coach more junior data scientists, raising the bar for analytical thinking and storytelling. Here's what we're looking for: * 10+ years of experience in Data Science at a product-focused software company. * Strong SQL and Python skills. * Proven ability to apply statistical methods, causal inference, and experimental design to real business problems. * Experience developing Machine Learning models is a plus. * Excellent communication skills, with a track record of influencing cross-functional stakeholders and leadership. * Demonstrated experience leading large, technically complex projects with clear business impact. * A proactive, resilient problem-solver who independently structures ambiguous problems into actionable insights. * Passion for mentoring others and raising the bar for data science craft across the team. * BS/MS/PhD in a quantitative field (Statistics, Economics, Computer Science, Applied Math, etc.) or equivalent industry experience. Our cash compensation amount for this role is targeted at $170,000/yr - $210,000/yr in Denver, $185,000/yr - $225,000/yr in Los Angeles, $200,000/yr - $240,000 for San Francisco, Seattle and New York. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

About the Role: We're hiring for a Senior Staff Product Designer to shape the future of Gusto's top-of-funnel experience on Gusto.com as part of the Growth Leads team. This is a rare opportunity to influence how hundreds of thousands of small businesses discover, learn about, and ultimately decide to try Gusto. You'll craft high-impact, top-of-funnel experiences that drive qualified leads and reflect Gusto's brand and values. As a key member of the Growth Leads team, you'll shape how new customers-from employers to accountants-discover and engage with Gusto across Gusto.com. You'll bring together visual and interaction design excellence, marketing and conversion sensibilities, and a systems mindset for CMS-driven platforms. In line with Gusto's goal of becoming an AI-native company, you'll explore how emerging AI technologies can enhance the design process, personalize customer experiences, and improve conversion through intelligence and automation. Whether it's using AI-assisted tools to accelerate experimentation, or designing responsible, transparent, and human-centered AI-driven surfaces, you'll help define what "AI-native" means in the context of growth design. Working closely with Product, Engineering, Marketing, Brand, Content, and Data partners, you'll define strategy, execute high-velocity experiments, and design with empathy-ensuring our growth is both data-informed and customer-centric. About the Team: The Growth team at Gusto is responsible for the entire customer funnel-from the moment someone discovers Gusto, to deciding to use it, to onboarding, setup, and ongoing product adoption. Our work is grounded in a user-centric, value-led approach to growth that prioritizes trust, clarity, and long-term impact. As a key contributor, you'll collaborate with Engineers, Product Managers, Data Scientists, and strategic partners across Marketing and the business to shape critical moments across the customer journey-including top-of-funnel experiences on Gusto.com. Here's what you'll do day-to-day: * Drive the end-to-end design strategy and execution across Gusto.com and other top-of-funnel touchpoints, including campaign-driven experiences. * Lead vision work to evolve the Gusto.com experience, balancing long-term strategic thinking with iterative improvements that drive immediate impact. * Craft elegant, conversion-optimized user experiences that clearly communicate Gusto's value proposition and build trust with diverse audiences. * Design for modularity and scale, balancing compelling brand storytelling with CMS and system constraints. * Drive personalized, high-impact user journeys tailored to varied customer segments and needs. * Partner with Marketing, Product, Engineering, and Data to craft and test data-informed hypotheses and launch rapid, iterative experiments. * Develop and execute experimentation programs to optimize user flows and inform decisions at scale. * Stay ahead of how AI is transforming organic search and discovery, evolving Gusto.com's architecture and content strategy to remain optimized for SEO and localized (GEO) behaviors. * Leverage AI-assisted tools and insights to prototype faster, surface opportunities, and design personalized experiences that improve conversion. * Collaborate with cross-functional partners to define responsible, transparent, and human-centered uses of AI in growth and acquisition experiences. * Explore and prototype AI-enhanced CMS workflows that enable dynamic content creation, intelligent segmentation, and faster test iteration. * Evolve Gusto's design system and brand language to support intelligent, adaptive experiences-balancing automation with human creativity and craft. * Advocate for customer-first, empathetic design thinking that supports trust-centered growth. * Mentor and uplift designers across the Growth team-fostering craft, experimentation, and AI fluency across design practice. Here's what we're looking for: * 10+ years of product design experience with a strong focus on growth, marketing, funnel optimization, and crafting top-of-funnel experiences. * A portfolio that showcases elegant, high-conversion design work across web and responsive surfaces. * Proven ability to design for CMS-driven systems, modular frameworks, and complex, interconnected product experiences. * Deep understanding of information architecture, UX best practices, and service design principles-especially for lead generation and content-heavy surfaces. * Strong visual craft with a sharp eye for layout, hierarchy, and brand storytelling. * Demonstrated ability to translate user research and data into clear, actionable design solutions. * Experience defining and prioritizing high-impact design work in collaboration with cross-functional teams. * Fluency with modern AI and design tools (e.g., AI-assisted prototyping, generative content systems, predictive analytics) or a strong desire to learn and experiment with them. * Ability to connect emerging AI capabilities to business and customer value-balancing innovation with ethical and transparent design practices. * Curiosity and self-motivation to explore how AI can accelerate creativity, experimentation, and customer understanding. * Strong communication and collaboration skills, with a low-ego, team-first mindset. * Comfortable working in ambiguity and driving progress in fast-paced, iterative environments. * A track record of mentoring and coaching designers to elevate team-wide design quality. At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto's compensation philosophy and benefits offerings please view our Total Rewards Approach page. Our cash compensation range for this role is $172,000/yr to $215,000/yr in Denver & most remote locations, and $202,000/yr to $253,000/yr in San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: Gusto is actively searching for a dynamic and inspiring commercial P&C insurance sales leader to further accelerate Gusto's growth in the business insurance space. You will be responsible for driving new revenue by cross selling Gusto's insurance solutions to both prospects and our existing client base, with a focus on Commercial Property & Casualty policies. The pace in Gusto sales is fast and the landscape we're playing in is ever-changing. We're looking for someone who is motivated by that and who will bring their experience, creativity, and passion for empowering sales professionals to the table every single day. You align with our company values and have a knack for building for the long haul. If you're passionate about developing people, shaping processes, and you're excited to roll up your sleeves and lead by example, let's talk. About the Team: You will initially manage one licensed P&C sales agent hired for this critical pilot, with a path to leading a larger team in the near future. This team is central to evolving Gusto's business insurance strategy and is crucial to solving customer experience gaps and optimizing our offline insurance channels. Your team will serve as Subject Matter Experts (SMEs), performing the "human-in-the-loop" workflows required to train and optimize the AI Insurance Advisor, Gus. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot and the team you lead being key to establishing our digital insurance agency and licensed agent integration. Here's what you'll do day-to-day: Lead a team of P&C sales advisors to achieve and exceed weekly/monthly/quarterly targets for P&C policies. Encourage and empower your team to perform to their full potential. Build a world-class consultative sales team by investing in and developing the existing sales team while at the same time attracting top sales talent to Gusto. Coach and support the team in their role as subject matter experts (SMEs) providing "human-in-the-loop" support to optimize the AI Insurance Advisor, Gus, and assisting customers with complex P&C needs. Collaborate with Sales, Marketing, and Product leadership to identify market opportunities, drive leads and pipeline progression, and help shape the product vision and strategy. Use data to inform decision-making and focus areas - ranging from advisor skill development (e.g., coaching conversations, email campaign usage) to team initiatives (e.g., staffing to seasonality, piloting new activities). Track, measure, and report-out on sales effectiveness against targets and adjust programs and strategies as necessary. Build a culture of fun and excellence within the team. Cultivate each individual's skill set development and guide career pathing as they grow within the organization. Ensure the team maintains compliance with all state licensing and continuing education (CE) requirements for P&C insurance. Here's what we're looking for: P&C Insurance Expertise: 4-6 years of experience as a national producer for the small commercial P&C market Management Experience: 3+ years of people management experience in a sales organization. Licensing: An active Property & Casualty insurance producer's license, or the ability to obtain upon hire. Results-Oriented: Consistent track record of establishing and exceeding measurable goals. Sales Acumen: Experience with start-up environments and SMB SaaS sales models, and excellent working knowledge of inbound and outbound SaaS sales methodologies. Coaching Passion: A passion for coaching advisors on discovery, objection handling, and soft skills. Collaboration: Ability to interact effectively with multiple teams; excellent social and interpersonal skills. Education: Bachelor's degree from an accredited university. Technical Proficiency: Working knowledge of carrier quoting systems, proficiency in insurance software, and Salesforce.com (SFDC) experience required. Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving. Our cash compensation amount for this role is $143,675 to $176,000 OTE for Denver, Atlanta, Chicago & Las Vegas. $163,265 to $200,000 OTE for San Francisco & New York. $126,530 to $155,000 OTE for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: Are you a tax credit expert with a passion for helping small businesses? Join our Tax Credits team and shape the future of tax credit software. Your talents will be instrumental in delivering an exceptional customer experience for small businesses uncovering lucrative tax credits. You'll work directly with taxpayers, develop processes that enable our customers and teams, and use your knowledge of credits & customer interactions to inform technology developments. This is an exciting opportunity to join a dynamic team and make a real impact on small businesses all across America. About the Team: The Tax Credits team is on a mission to democratize tax credits and grants. We aim to make access to tax credits and grants ubiquitous for SMBs & business advisors, ensuring every business receives the financial support they deserve to fuel growth, innovation and long-term success. The Tax Credits Operations team is a collaborative team who are passionate about tax credits. As a member of the Operations team at this stage in our journey, you will be a customer advocate and educator, simplifying a small business's experiences with tax credits. As a tax credits operator and expert, you'll have the opportunity to work directly on components of each customer's credit and use your experience to shape the direction of our product, process, and tools. Here's what you'll do day-to-day: Serve: Proactively & reactively resolve complex customer inquiries related to tax credits (e.g. R&D) Take ownership of customer outcomes, ensuring small businesses get great value out of the tax credits products that Gusto offers Educate: Educate yourself and others on tax credits, including R&D tax credits, 401K, WOTC, and other relevant incentives Operate: Roll up your sleeves and complete or quality control behind-the-scenes tasks (e.g. data review, calculations, uploads) that result in high quality credit forms and documents Develop: Create and inform solutions alongside the Tax Credits technical (EPDD) and service (ES, CX) teams Continuously improve and iterate on processes and approach Collaborate: Work with team members to find creative customer solutions that are compliant and sustainable Partner across teams to inform and build tax credits product, process, and tools Here's what we're looking for: Service: A minimum of 2 years in a customer-facing role, ideally at a technology, tax, or financial services company Tax or Tax Credits skills: A minimum of 2 years experience with tax, tax preparation, or tax credits. Audit experience is a bonus! Communication: You have strong experience communicating with customers, and are passionate about advocating on their behalf. You can break down complex concepts into concise and simple messages. Detail Orientation: You pay attention to details, take pride in your work, and understand how the quality of your work product quality impacts small business finances. Critical Thinking: You seek to understand the root cause of customer and process issues and are able to identify trends. You attempt to resolve trending issues with the appropriate level of urgency. Proactive Problem Solver: You are always looking for ways to improve processes, solve customer issues more efficiently, or prevent issues from popping up Systems Knowledge: You have supported a technical or complex product or service. You may have used ticketing tools (e.g. HubSpot, Salesforce) previously and you are able to leverage them to solve complex customer issues. Change Agent: Suggest, drive, and embrace changes and iterations. Seek opportunities to challenge and improve the status quo. AI: AI-forward mindset, with experience exploring and incorporating AI into how you work. Compensation: Our cash compensation amount for this role is $78,300 to $92,000/year in Denver, and $97,870to $115,000 for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: The Senior Manager, CX L&D Readiness is the architect of an AI-powered readiness ecosystem across all CX teams - including Customer Care, Benefits Operations, and Payroll Operations. You'll redefine how Gusto delivers readiness, integrating automation, adaptive learning, and data-driven coaching to accelerate time-to-proficiency, strengthen QA outcomes, and scale performance support across thousands of advocates. You'll architect Gusto's AI-Native Readiness strategy defining how GenAI, adaptive simulations, and predictive learning agents reshape skill development and performance support. You'll apply principles of data integrity, feedback loops, and Responsible AI to ensure learning at scale is both personalized and ethical. Here's what you'll do day-to-day: Advocate & Customer Experience Own readiness end-to-end, ensuring advocates are confident and competent as they transition from onboarding to production. Extend readiness into ongoing upskilling and reskilling, helping teams adapt as products, skills, and AI tools evolve. Partner with QA, WFM, and CX Operations to align readiness with performance metrics like QA scores, first-contact resolution, and handle time. Deploy AI-assisted coaching flows that identify learning gaps and surface “next best actions” for advocates and managers. Collaborate with Voice of the Customer and Process Improvement teams to identify friction points and build AI-informed interventions that improve both Gustie and Gustomer experiences. Learning Strategy & Execution: Design adaptive readiness journeys powered by AI adjusting practice sets, simulations, and job aids in real time based on performance data. Use predictive analytics and readiness dashboards to anticipate risk, target interventions, and optimize ramp time. Automate the content workflow: leverage AI to draft, version, and QA readiness materials, freeing designers and facilitators for high-impact work. Partner with L&D peers to create an AI-ready content structure (modular, tagged, and retrievable) that powers learning in the flow of work. Create evaluation plans for AI features that include accuracy checks, bias and safety reviews, and business impact metrics. Standardize readiness playbooks, curricula, and QA checkpoints across CX. Leverage AI agents and adaptive learning to deliver just-in-time support, personalized readiness interventions, and data-driven insights at scale. Own the experimentation pipeline for new AI-powered readiness features, using A/B testing and rapid iteration to measure improvements in time-to-proficiency (TTP) and QA performance. Establish standardized prompt design and retrieval practices to ensure high-quality, bias-mitigated outputs across readiness agents. Team Empowerment: Lead, coach, and develop a team of Readiness leaders (PEs) to operate as AI-native enablement professionals. Foster experimentation with AI tools from prompt-driven design to workflow automation anchored in data accuracy, ethical use, and business value. Build career paths and skill development opportunities within the team. Build psychological safety for innovation, encouraging iteration and visible learning around what works and what doesn't. Cross-L&D Collaboration: Partner with Instructional Design on aligning readiness content with curricula and create AI-ready content structures that improve retrieval quality. Partner with Facilitation & Programs to ensure a seamless hand-off between onboarding and readiness. Partner with Learning Strategy & Ops to measure readiness impact, build dashboards and review cadences that separate vanity metrics from true proficiency gains to inform CXLT-level decisions. Partner with Product and Engineering to support the adoption and continuous improvement of AI tools for customer facing employees. Share best practices and insights across the broader Gusto L&D community. AI and Automation: Treat AI as an amplifier of human enablement, not a replacement for it. Drive the roadmap for AI-powered delivery, QA augmentation, and learning automation from scoping pilots to scaling successful use cases. Establish rigorous evaluation criteria for AI use: accuracy, bias, safety, latency, and relevance. Partner with Security, Legal, and People Tech to ensure compliance and responsible data handling. Define metrics that prove business value faster ramp, reduced QA fallout, improved readiness survey scores, and higher retention. Implement and govern Responsible AI frameworks for readiness agents, including bias detection, accuracy audits, and opt-out pathways. Here's what we're looking for: 7+ years leading readiness, enablement, or L&D programs in a complex, high-growth environment. 3-6 years managing operations, technology, or enablement teams. Demonstrated success scaling AI-powered learning or workflow automation with measurable impact. Strong grounding in learning science, coaching, and adult development. Proven ability to connect learning initiatives to operational outcomes (QA, retention, ramp time, deflection). Expertise in using or managing AI tools for content generation, data synthesis, QA support, or adaptive learning. High data literacy and comfort building dashboards or working with readiness analytics. Ability to translate ambiguous opportunities into experiments with clear success criteria. Exceptional communication and stakeholder management across technical and non-technical partners. Familiarity with LLMs (e.g., GPT-based systems) and their applications in learning or operational workflows. Experience defining or applying Responsible AI frameworks - accuracy, bias, latency, and safety reviews. Comfort leading through change with clarity, empathy, and strategic focus. Travel to our Customer Experience Hubs and vendor sites (Denver, Las Vegas, Phoenix, Chicago, Manila, Guatemala City) is expected ~30% annually, increasing to 50% during peak hiring or program launches. Our cash compensation range for this role is $140,815 to $183,060 in Denver, Chicago & Phoenix. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

About the Role: As a Staff Software Engineer on the Developer Productivity - Local Environments team, you will be a key player in defining, maintaining and enhancing the local development experience for our software engineering team. You will be responsible for ensuring environments are consistently working, troubleshooting issues, streamlining initial setups, and driving improvements to our tooling and processes. Crucially, you will also be exploring and implementing innovative ways to leverage Artificial Intelligence (AI) to further optimize our development environments and accelerate local development. You will collaborate closely with engineers across various teams to understand their needs and provide effective solutions, with a forward-thinking approach towards incorporating intelligent automation. About the Team: The Local Environments team, part of the Developer Productivity organization, is responsible for empowering our software engineers through consistent, reliable, and delightful local development experiences that maximizes engineering velocity and minimizes friction to shipping. We understand that a well-functioning local environment is crucial for productivity, innovation, and overall developer happiness. We proactively work to ensure environments are stable, easy to set up, and continuously improved, allowing our engineers to focus on building amazing software. Here's what you'll do day-to-day: * Identify opportunities for improvement and drive initiatives to enhance the efficiency and reliability of development environments with a focus on building faster developer feedback loops leveraging emerging AI technologies balanced with established practices and tool chains. * Contribute to the development and improvement of internal platforms and tools related to development environments. * Work closely with software engineers to understand their pain points and requirements related to local development. * Collaborate with other infrastructure and platform teams to ensure seamless integration of development environments with other systems. * Proactively monitor and maintain the health and stability of standard development environments. * Diagnose and resolve issues related to local setups, including operating system configurations, networking, dependencies, and tooling. Here's what we're looking for: * 10+ years of software development experience * Curiosity and ability to operate in an AI-native environment - integrating intelligence, automation, and experimentation to increase developer productivity through tooling and infrastructure enhancements. * Systems thinker with a strong ability to communicate effectively. * Comfortable with architectural thinking and delivering solutions through code. * Experience with Rails and Ruby, including developer tooling for large engineering teams. * Ability to work with colleagues as both customers and partners. * Active working knowledge and architecture experience with Ruby. * Experience with asynchronous processing using Sidekiq and/or Kafka. Our cash compensation amount for this role is targeted at $190,000/yr to $210,000/yr in Denver & most remote locations, and $220,000/yr to $250,000/yr in New York, Seattle & San Francisco Bay Area. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

About the Role: Gusto's Data team leverages Gusto's rich dataset to guide product direction and decision-making by building the right AI/ML solutions at scale. For this role, we are looking for a technical leader (an individual contributor) to drive the scale and optimization of our customer experience and customer journey via building AI and ML enabled experiences and services. In this role you will build and optimize AI/ML solutions and infrastructure that power our customer journey related products. You'll be working with a strong AI/ML team and seasoned leaders in Engineering, Product, Design, Data Science, Marketing, and Sales. In this role, you'll work cross functionally to build Platforms that span the entire breadth of the unified service platform stack using machine learning and AI to personalize world class content for our customers and enhance customer experience. Here's what you'll do day-to-day: * Design and develop scalable, production-grade AI and machine learning models for solving complex business problems. * Lead and mentor teams of ML engineers, fostering a culture of technical excellence and innovation. * Collaborate cross-functionally with product, engineering, and business stakeholders to identify AI opportunities and translate them into actionable solutions. * Stay current with latest AI research; prototype and implement new algorithms and advancements from academia and industry. * Oversee model validation, deployment, evaluation, and lifecycle management, ensuring robust monitoring, explainability, and performance. * Guide technical strategy, roadmap, and architectural decisions for the ML/AI function. * Communicate findings, roadmaps, and performance results clearly to executives and non-technical partners. Here's what we're looking for: * 8+ years' hands-on experience building and deploying end-to-end ML/AI systems in industry or academia. * Deep expertise in one or more advanced ML methods (supervised, unsupervised, reinforcement learning, deep learning, NLP, LLMs, RAG, etc.). * Proven track record of delivering large, impactful ML/AI projects into production environments. * Proficient in modern ML frameworks (TensorFlow, PyTorch, HuggingFace, etc.) and cloud computing platforms (AWS, GCP, or Azure). * Strong programming skills in Python and familiarity with best engineering practices (CI/CD, testing, code review). * Demonstrated leadership in cross-disciplinary teams and ability to mentor scientists and engineers. * Excellent communication skills and business acumen. * Ph.D. or Master's degree in Computer Science, Machine Learning, Statistics, Mathematics, or a related field is a plus. Our cash compensation amount for this role is targeted at $230k-280k for San Francisco, New York, and Seattle $205k - 255k in Los Angeles, $185k-234k in Denver, and 200k-250k CAD for Toronto. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role We're looking for a visionary Senior Manager, Contracts Management and Operations to lead the next evolution of how contracting happens at Gusto. This role goes far beyond contract review - it's about re-designing how contracting happens at Gusto, using cutting-edge AI technology and systems, process design, and change leadership to create scalable, intelligent systems. In this role, you will own Gusto's vendor contracting process end-to-end, while driving AI-focused transformation across contract operations. You will set the standards, playbooks, and tooling that allow Gusto's commercial legal function to scale with speed and intelligence as the company grows. You'll be the driver of innovation: determining thresholds for review, implementing smarter ways of working, and leading the way in educating our legal team-and the business at large-on new industry practices and breakthroughs in smarter contracting. If you're energized by leading change, experimenting with new technologies, and building a model for how in-house legal teams can thrive in the AI era, this is your opportunity to make a lasting impact. About the Team The Legal & Compliance team partners with Gusto teams to enable innovation, facilitate responsible company growth, accelerate the Gusto roadmap, and provide compliant products to our customers, through solution-focused counsel on legal and business risks. We are passionate about using groundbreaking technology and excellent service to elevate the experience of small business owners and their employees. Each team member is a true owner and makes a tremendous impact every day. The Commercial Legal team is at the forefront of that mission. We're responsible for contracting, procurement enablement, and designing the contracting processes, playbooks, and terms frameworks that allow Gusto to grow responsibly at scale. We combine legal judgment, process mastery, and forward-looking technology to do our jobs smarter and better every day. You'll be joining a team of true owners who thrive on impact-and you'll play a critical role in taking us into the next generation of commercial legal. Here's what you'll do day-to-day Lead Contract Operations Strategy Define and execute the long-term vision for contract management and operations, aligning process excellence, technology, and stakeholder experience. Drive change management initiatives that reshape how Gusto teams engage with contracts. Serve as the bridge between Legal, Procurement, Security, & Engineering to ensure our contracting infrastructure scales intelligently with Gusto's growth. Reimagine the Vendor Contracting Process Own Gusto's high-volume vendor contracting pipeline-not just by reviewing and negotiating contracts, but by designing and implementing smarter processes that keep pace with a fast-growing business. See the vendor queue as a system to optimize, using thresholds, playbooks, and tooling to separate the routine from the high-risk. Define smart risk taking principles that balance consistency and speed, ensuring contracts move through review and approval quickly while still protecting the company. Partner closely with Procurement, Privacy, Security, and other Third Party Risk Management stakeholders to define SLAs and deliver a scalable process. Design the Playbooks & Standards Develop and refine templates, playbooks, and approval flows that make our processes faster, smarter, and repeatable. Drive efficiency across procurement and cross-functional teams by embedding scalable workflows. Report regularly on metrics-AI adoption, cycle times, execution rates-demonstrating how Commercial Legal accelerates company goals. Pioneer AI & Digital Transformation in Contracting Architect and own the roadmap for contract lifecycle management (CLM), AI review tools, and data systems (we currently use Ironclad and GCAI). Identify, pilot, and integrate emerging technologies that automate low-risk contracts, augment legal decision-making, and ensure the Commercial Legal team is always on the leading edge of contracting innovation. Data & Insight-Driven Culture Build a metrics-first culture-develop KPIs, dashboards, and insights that track contracting efficiency, risk exposure, and business impact Translate analytics into clear narratives that show how Commercial Legal accelerates company growth. Team Influence & Education Champion change by training cross-functional partners on new tools and processes. Be the voice of innovation across Legal, showing what an AI-empowered legal function can achieve. Position Gusto as a model of how legal functions can scale and innovate in an AI-powered world. Here's what you'll need for this role Bachelor's degree. 7+ years of experience in contract management, commercial contracting, or vendor contract review and negotiation (in-house strongly preferred). Proven ability to take ownership of high-volume contracting pipelines and turn them into well-oiled, scalable systems. Hands-on expertise with contract lifecycle management systems and AI-powered contract review tools. Demonstrated success building and improving processes, not just running them. A builder's mindset-hungry to experiment, optimize, and deliver measurable results. Exceptional communication skills and the ability to influence and inspire stakeholders across legal, procurement, and the business. A passion for showing that Commercial Legal is a driver of innovation and business impact, not a blocker. Here's what we'd love to see you bring to the table A passion for AI and technology as drivers of legal transformation. Experience reporting on contract repository adoption, metrics, and operational KPIs. Familiarity with regulated industries (e.g., financial services, payroll/tax SaaS, healthcare). Creative problem-solving skills and the confidence to take smart risks. Energy, curiosity, and a drive to be part of something groundbreaking. A team-first approach, with no job too big or too small. Compensation Our cash compensation amount for this role is between $113,190 - $133,000/year in Denver and between $132,765 - $156,000/year for New York/San Francisco. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: The Senior Leader, Benefits Advising will empower Gusto's licensed advising renewal organization, ensuring our customers offer the best health insurance and benefits offerings for their employees. This role will balance both customer impact and operational excellence: you'll be responsible for building mechanisms that drive customer retention, expansion, and exceptional customer experience at scale. This role will be at the forefront of helping integrate AI and automation into the advising experience, ensuring our teams leverage technology responsibly while maintaining the human touch that builds trust with small business owners. About the Team: Your team will support small business owners in accessing the best health insurance and holistic benefits offerings - including ancillary coverage, tax-advantaged accounts, and retirement plans like 401(k). Much of this work is centered around small group health insurance, including fully insured and level-funded plans, where tailored guidance is essential for customer success. You'll directly empower a team of 4-6 frontline leaders and a total organization of 30-50 licensed advisors and specialists, guiding them through renewal cycles and enabling them to serve as trusted advisors to our customers. Here's what you'll do day-to-day: Directly oversee and develop leaders: Coach and empower 4-6 leaders and their teams of licensed advisors. Lead CX strategic direction: Define and execute the renewal and advising strategy for Gusto's benefits customers. Drive retention and revenue growth: Deliver on retention targets by ensuring tailored, high-quality renewal experiences. Build playbooks to expand coverage across ancillary, tax-advantaged, and retirement offerings. Partner with Finance and CX leadership to establish and achieve revenue goals tied to renewals. Redesign advisor workflows to integrate AI and automation tools (e.g., Salesforce, Next Best Action, AI-powered recommendations), enabling advisors to spend more time on high-value customer engagement while ensuring responsible AI practices and human-in-the-loop oversight for critical decisions Champion compliance, ethics, and trust, ensuring all advisor recommendations meet regulatory standards while maintaining customer-first outcomes.” Foster culture and engagement: Build a culture rooted in Gusto's values, creating an environment of trust, feedback, and continuous learning. Lead change management: Guide organization-wide improvements, enabling advisors and managers to adapt and thrive in a dynamic environment. Evolve the customer experience: Use customer feedback and data to refine renewal processes and deliver more holistic, outcomes-focused advising. Here's what we're looking for: 5+ years of leadership experience in customer success, account management, or benefits/insurance advisory, including leading leaders. Proven ability to drive revenue growth, customer retention, and expansion through consultative renewal and upsell strategies. Direct experience with small group health insurance (fully insured and level-funded models) is required. Background in building scalable processes and mechanisms to support customer outcomes. Ability to evaluate and adopt AI tools strategically to measurably improve advisor productivity, customer retention, and operational efficiency-while balancing innovation with risk management, compliance requirements, and maintaining customer trust in a licensed advisory context. Experience with technology/automation solutions such as Salesforce, APIs, and benefits administration platforms. Executive presence with the ability to align leaders across CX, Sales, and Product, and communicate a compelling vision to both frontline teams and senior stakeholders. Customer-first mentality with a first-principles-thinking approach. Thrives in a fast-paced environment with constant change and rapid growth. Able to make measured, objective, data-driven decisions on a daily basis. Our cash compensation amount for this role is $119,000/yearly to $154,000/yearly in Denver, Las Vegas, Chicago, Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: At Gusto, the People team is the foundation of everything we do. Recruiting is core to our ability to grow, innovate, and serve our customers. As a Senior Recruiting Manager, you'll lead, empower, and develop a team of recruiters while partnering closely with senior business leaders to shape hiring strategy. This role is more than leadership-it's an opportunity to influence and evolve how we operate as a recruiting team & driving proactive, creative, and data-informed strategies that balance high-volume hiring with targeted, niche searches. You will directly influence how Gusto scales our CX (Customer Success) or GTM (Go-To-Market) organizations ( yes, we are hiring TWO roles!) and create a recruiting model that will fuel our business well into the future. About the Team: The Recruiting team at Gusto (also known as Invite) is a dynamic, forward-thinking group focused on bringing world-class talent. We innovate on sourcing, create strong partnerships with the business, and lean into creative approaches that ensure an outstanding candidate experience. We believe in building trusted relationships, driving measurable results, and continuously improving how recruiting supports Gusto's growth. Here's what you'll do day-to-day: Lead & Empower: Manage and develop a team of recruiters supporting CX or GTM hiring needs, from high-volume frontline roles to specialized, senior-level searches. Strategic Partnering: Act as a trusted advisor to senior leaders, aligning hiring strategies with business goals, customer outcomes, and workforce plans. Program Building: Design and implement scalable recruiting programs that support long-term growth while fostering innovation and creativity in pipeline generation. Data & Insights: Build and leverage data infrastructure to forecast capacity, shape sourcing strategies, and influence executive decision-making with compelling insights. Innovation & Emerging Technologies: Experiment with new sourcing strategies, employer brand approaches, and tools-including AI-to elevate how we attract top talent, improve efficiency, and increase recruiter productivity. Team Development: Empower recruiters through coaching, development plans, and clear frameworks for growth, while removing roadblocks to execution. Business Impact: Ensure recruiting strategies directly drive business outcomes and customer impact, enabling Gusto to scale with speed and quality. Here's what we're looking for: 10+ years of recruiting experience, including 7+ years leading people in high-growth, scaling environments (tech or startup preferred). Experience managing a team of 8+ recruiters across levels, with proven success balancing high-volume hiring and niche, senior talent searches. Deep craft expertise with a track record of building programs, pipelines, and practices that drive scalable and sustainable results with an ability to iterate over time and changes. Curiosity and proven ability to learn and apply AI-driven tools to improve operational efficiency and recruiting effectiveness; not an expert, but eager to experiment and adopt innovations that drive impact. Hands-on leader who thrives in the trenches with their team while setting clear strategic direction. Strong analytical skills; able to use data for capacity modeling, sourcing strategies, and investment planning-plus the storytelling ability to influence senior executives (VP and above). Proven ability to build inclusive, creative, and high-performing recruiting teams. Executive presence and communication skills, with a business-forward mindset that connects hiring strategies to business leaders' goals, customer impact, and revenue growth. Energized by the opportunity to rebuild, innovate, and leave a lasting mark on Gusto's talent strategy. Our cash compensation amount for this role is $165,000 to $205,000 in Denver & most major metro locations, and $193,000 to $240,000 for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: As the Enterprise Applications AI Architect, you will lead the integration of AI and automation across Gusto's enterprise applications ecosystem, transforming how internal systems connect, communicate, and operate. Sitting within the IT and Enterprise Applications organization, you will partner closely with Product, Engineering, Finance, People Tech, and Operations to bridge business needs with AI driven solutions. You will act as the connector between business requirements and AI frameworks, designing Model Context Protocols (MCPs) and AI agents that make enterprise workflows smarter, faster, and more autonomous. In line with Gusto's FY26 Enterprise Systems strategy, you will help shift our ERP and Finance systems from reactive workflows to predictive, context aware, and self improving platforms, while ensuring security, compliance, and measurable impact. This role combines hands-on technical execution with strategic systems thinking, using integration fluency, AI literacy, and business empathy to create the connective tissue that allows AI to seamlessly augment enterprise operations. About the Team: This role will report to the Enterprise AIT team, a group focused on driving the intelligent transformation of Gusto's enterprise systems. The Enterprise AIT team is responsible for integrating AI, automation, and advanced analytics across our internal applications ecosystem to improve scalability, efficiency, and decision-making. Partnering closely with Finance, Business Ops, IT, and Security, the team enables Gusto's enterprise systems to become smarter, more predictive, and more adaptive. This is a new role, designed to expand the team's capacity to operationalize AI within enterprise workflows and support Gusto's broader Enterprise Systems strategy. Here's what you'll do day-to-day: Translate business needs into AI workflows by partnering with Finance and Business Operations teams to identify automation opportunities and design agentic workflows that improve decision making and reduce manual effort. Develop and maintain Model Context Protocols (MCPs) that securely and reliably connect enterprise systems such as NetSuite, Zuora, and Jira to AI agents, with clear documentation and optimization. Create and manage intelligent agents that execute or augment core enterprise processes such as onboarding, billing support, and compliance monitoring using large language models and orchestration frameworks. Govern the full lifecycle of MCPs and agents, ensuring adherence to enterprise data governance, privacy, and security standards, including SOX compliance, auditability, and appropriate access controls. Measure and optimize impact by defining and tracking KPIs such as automation adoption, efficiency gains, agent accuracy, reliability, and cost performance, and using those insights to guide iteration. Enable and influence the organization by partnering with IT, Security, and business stakeholders to build reusable AI frameworks, coach teams on safe and effective AI driven workflows, and champion AI first practices across day to day operations. Here's what we're looking for: 8+ years in Business Systems Analysis, Enterprise Applications, or Automation roles, with a track record of delivering impact in complex environments. Demonstrated experience building and maintaining integrations across systems such as Jira, NetSuite, or similar, with a strong grasp of APIs, JSON, and RESTful service design. Hands-on knowledge of AI agent frameworks (for example LangChain, CrewAI, Semantic Kernel, MCP) and experience designing or maintaining Model Context Protocols or equivalent frameworks. Familiarity with leading LLM platforms (OpenAI, Anthropic, Gemini etc.) and practical experience with prompt engineering. Proficiency in Python or JavaScript for automation, orchestration, and building modular, scalable AI workflows that translate complex requirements into executable solutions. Strong documentation, analytical, and stakeholder communication skills, with the ability to clearly explain tradeoffs and align technical solutions with business needs. Passion for building secure, compliant, and explainable AI systems, embedding risk, privacy, and compliance considerations (including SOX and audit controls) into every solution, with a growth mindset and focus on clarity, iteration, and measurable outcomes. Our cash compensation amount for this role is targeted at $150,000-$165,000 /yr in Denver & most remote locations, and $185,000-$205,000 /yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: We're looking for an AI-focused Head of Sales and GTM Operations to lead the transformation of Gusto's revenue engine into an AI-first operating model. This role will oversee a team of AI Agent Builders and operations leaders who are redefining how Sales, Marketing, and Partnerships work at scale-replacing manual processes with intelligent automation, enhancing decision-making with AI-powered insights, and building the infrastructure for autonomous revenue operations. This is a rare opportunity to lead both the strategic vision and execution of AI transformation across GTM. You'll build and scale a high-performing team that designs, deploys, and optimizes AI agents and workflows that drive measurable revenue impact. Reporting into the Head of Revenue Operations, you'll partner directly with the CRO and executive leadership to architect the future of how Gusto sells, markets, and grows. About the Team: The Revenue Operations team is the connective tissue between strategy, systems, and execution across Gusto's Go-to-Market (GTM) organization. We enable Sales, Marketing, and Partnerships to operate efficiently, make data-informed decisions, and deliver exceptional experiences to customers and partners. As Gusto embraces an AI-first future, this team is building the infrastructure, workflows, and evaluation frameworks that power intelligent, high-performing GTM operations. You'll collaborate closely with RevOps, Data, BizTech, and GTM leadership to bring automation and AI to life across our revenue systems and processes. Here's what you'll do day-to-day: AI Strategy & Vision: Define and execute Gusto's comprehensive AI-native GTM operations strategy. Set the roadmap for AI adoption across sales productivity, marketing personalization, partner operations, and customer intelligence. Drive technology selection, vendor partnerships, and build-vs-buy decisions that balance innovation with scalability. Team Leadership: Build, lead, and mentor a team of AI Agent Builders, automation engineers, and RevOps specialists. Foster a culture of experimentation, rapid iteration, and measurable impact. Develop talent that can translate complex business problems into elegant AI-powered solutions. Agent & Automation Architecture: Oversee the design and deployment of agentic systems and intelligent workflows that automate manual GTM processes. Establish governance frameworks, evaluation standards (prompt reliability, latency, cost, business impact), and best practices for safe, scalable AI deployment across revenue teams. AI Infrastructure & Integration: Lead the technical architecture connecting Salesforce, GTM tools, data warehouses, and AI platforms into a unified, intelligent revenue system. Ensure data quality, system reliability, and seamless integration across the revenue tech stack. Revenue Operations Excellence: Maintain operational excellence in territory design, quota setting, pipeline management, forecasting, and compensation-while progressively embedding AI capabilities that enhance efficiency, accuracy, and strategic insight. Cross-Functional Leadership: Partner with Sales, Marketing, Partnerships, Growth, Finance, Data, and Product teams to identify high-impact automation opportunities. Drive alignment on trade-offs, prioritization, and resource allocation. Translate business needs into technical requirements and AI capabilities into business value. Change Management & Adoption: Champion AI adoption across GTM teams through training, enablement, and change management programs. Ensure every AI initiative ships with clear ownership, measurable outcomes, and user feedback loops. Performance & Impact Measurement: Build comprehensive frameworks to measure AI/automation ROI-tracking productivity gains, conversion lifts, time saved, cost efficiency, and revenue acceleration. Use data to continuously optimize and prioritize AI investments. Market Intelligence & Innovation: Stay at the forefront of AI/ML developments in revenue operations. Evaluate emerging technologies (LLMs, AI agents, automation platforms) and determine how Gusto can leverage or build competitive advantages through AI-native operations. Here's what we're looking for: 10+ years of progressive experience in GTM Operations, Sales Operations, or Revenue Operations, with at least 5+ years in a leadership role building and scaling high-performing teams in high-growth SaaS environments 2-3 years of hands-on experience leading AI/automation initiatives, building agent-based systems, or transforming operations through intelligent automation Deep expertise in CRM systems (e.g., Salesforce) and revenue technology stacks, with demonstrated ability to architect AI integrations, automation workflows, and system integrations across data warehouses and GTM tools Strong understanding of AI/ML concepts, LLMs, agentic systems, and modern AI tooling-able to evaluate technical trade-offs, guide build-vs-buy decisions, and translate AI capabilities into business value Exceptional ability to build, mentor, and scale technical operations teams working at the intersection of AI, automation, and business systems-fostering cultures of experimentation and measurable impact Proven track record of driving organizational change and AI adoption across multiple stakeholder groups, with excellent communication skills to influence executive audiences Exceptional analytical skills with ability to define success metrics for AI initiatives, measure ROI (productivity gains, conversion lifts, cost efficiency), and use data to optimize investments Strong program management skills to balance multiple complex initiatives, drive cross-functional alignment, and deliver measurable progress in fast-paced environments Deep understanding of the entire revenue lifecycle and how AI can enhance each stage, from demand generation to customer retention Bachelor's degree in Business, Computer Science, Engineering, or related field (MBA or technical graduate degree is a plus); AI-native mindset that sees automation as the default and is passionate about making humans more effective through intelligent systems. Compensation Our annual base salary compensation range for this role is $240,000 - 270,000 in San Francisco & New York, and $204,445 - $230,000 in Denver & Atlanta. This role is also eligible for an annual variable cash bonus (up to 20%). Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff-like payroll, health insurance, 401(k)s, and HR-so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. About the Role: We are seeking a highly motivated and licensed Property & Casualty (P&C) Insurance Broker to join our team as part of a critical pilot to launch a P&C broker model at Gusto. You will be essential in evolving Gusto's business insurance channel by acting as a licensed agent to quote and issue business insurance policies with our NEXT Insurance carrier partner. You will use your expertise to provide direct support and an improved experience for small business customers with complex insurance needs, helping to capture meaningfully higher revenue and accelerating the development of our AI Insurance Advisor. About the Team: You will be one of two licensed commercial P&C sales representatives hired for this pilot. This team is crucial to solving customer experience gaps and optimizing our offline insurance channels. You will be a SME who is part of the "human-in-the-loop" workflows required to train and optimize Gus as an AI insurance advisor. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot being key to establishing our digital insurance agency and licensed agent integration. Here's what you'll do day-to-day: Make outbound dials to prospective and existing small business clients to assess their complex P&C insurance needs and recommend suitable coverage options. Quote and issue Property & Casualty policies, primarily with the NEXT Insurance carrier, in our offline sales channel. Achieve required daily, weekly, and monthly sales activity expectations. Provide human-in-the-loop support to optimize the AI Insurance Advisor, Gus, and assist customers with more complex needs. Maintain client relationships, manage policy renewals, and facilitate changes or endorsements to existing policies. Act as a trusted liaison between clients and carriers, including assisting clients with reports of losses and claims settlement when necessary. Actively work to cross-sell and up-sell additional P&C lines of coverage and strive to achieve monthly production goals for units and/or revenue. Maintain accurate and up-to-date client records and policy documentation within CRM systems (SFDC workflow). Stay current on industry trends, products, regulations, and underwriting guidelines to provide accurate advice and ensure compliance. Here's what we're looking for: Experience in the field: Proven experience in insurance sales or brokerage, with coverage level knowledge of commercial P&C products (e.g., Workers' Compensation, BOP, Commercial Auto, E&O). [2 years] Licensing: An active Property & Casualty insurance producer's license, or the ability to obtain upon hire. Communication & Interpersonal Skills: Excellent verbal and written communication, active listening, and strong interpersonal skills to build rapport and explain complex concepts clearly. Sales & Negotiation: Strong sales and negotiation abilities with a proven ability to meet sales targets. Technical Proficiency: Working knowledge of carrier quoting systems, proficiency in insurance software, and familiarity with CRM systems like Salesforce (SFDC). Mindset: A demonstrated passion for delivering an incredible customer experience and genuine empathy for small business owners. Attributes: Highly self-motivated, goal-oriented, and an entrepreneurial ownership mentality to thrive in a fast-paced, high-energy environment. Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving. Our cash compensation amount for this role is $102,040 to $125,000 OTE for Denver, Atlanta, Chicago & Las Vegas. $123,265 to $151,000 OTE for San Francisco & New York. $95,510 to $117,000 OTE for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.