By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners — owning an entire roadmap end to end and shipping product all the way from strategy through to the nitty-gritty details (some describe this kind of role as a “GM” type role).
• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team

We have a clear vision for how AI-powered tools will transform HR for small businesses, and we're looking for a Senior Product Manager to make it real: sharpen priorities, own outcomes, and partner deeply with engineering and design to ship products that matter.

Document Studio is one of our most ambitious product bets: an experience that helps small business owners navigate the hard HR decisions, a new hire, a compensation change, a difficult termination, and generates the right documentation, personalized to their situation, compliant with their state, reflecting how they want their culture and values to come through, backed by rules they can trust.

The foundation is in early stages: a Handbook product is in beta, and the internal platform is an MVP. Our ambition is considerably bigger than what's been built. The customer experience is still evolving: what it looks and feels like to be guided through a termination, a comp change, or a new hire without needing to be an HR expert. The scale is real: employment law varies across all 50 states, and the content pipeline has to handle that without becoming a bottleneck. And the internal engine, the rules and content infrastructure that makes trusted output possible, is still being defined. This is one of Gusto's most ambitious bets, and the person who takes this role will shape it.

You'll own that end-to-end: Handbook, document templates, an employer-facing document manager, the employee experience on the other side of those documents, and the underlying platform that powers all of it. These documents serve two audiences: they help employers navigate decisions and set expectations, and they're how employees learn what's expected of them and experience HR at their company.

Your engineering and design partners are experienced builders who want to co-define what gets built. You'll work closely with Legal and Compliance and our HR experts to turn their expert knowledge into guided document-creation experience, and with the broader team to connect Document Studio to the rest of what Gusto is building for small businesses. We need a PM with strong product craft, real AI product experience, and the ability to push creative boundaries while executing quickly.

Here’s what you’ll do day-to-day: 

• Own product strategy and roadmap for the Document Studio platform—Defining the vision, making hard prioritization calls, and ensuring we’re building the right things for customers.
• Work side by side with engineering and design: clarify problems, frame opportunities, and shape solutions together rather than handing over finished specs. You’ll be a true partner, not a ticket-writer.
• Drive discovery and validation with customers and our internal experts—synthesize feedback, identify patterns, and turn insights into clear requirements and success criteria.
• Define and track outcomes (usage, quality, efficiency, business impact) and use data to inform what we build next.
• Operate in ambiguity: our roadmap is evolving, the AI landscape is moving fast, and the “right” product isn’t always obvious. You’ll help the team navigate that uncertainty with structure and judgment.
• Think creatively about AI-native experiences, beyond chatbots and forms. The bar here is high: outputs need to be accurate (HR has real compliance stakes), tailored to each customer's situation, and genuinely useful rather than generic. 

Here’s what we're looking for: 

• 5+ years of product management experience. You have a track record of owning significant product areas and shipping outcomes in fast-moving environments. Ideally with additional experience in roles that involve helping people navigate choices they don't have the domain knowledge to make confidently
• AI product experience. You've shipped AI products where getting it wrong has real stakes — and you understand when AI adds value. You understand how to scope AI capabilities, manage uncertainty, and design for human-in-the-loop. 
• Strong product craft. You’ve shipped products that users love and that moved the needle. You’re rigorous about problem definition, scope, and success—and you know when to simplify or cut. 
• Platform and systems thinking. You identify the generalizable structure underneath multiple use cases and build toward it. Experience in any domain where structured logic needs to scale — compliance, legal, financial, medical, pricing, knowledge infrastructure — matters more here than document-specific background.
• Cross-functional collaboration. You've collaborated with domain experts to shape product experiences and build always-on processes.
• Technical fluency. You can have real conversations with engineers about AI systems, rules engines, and content infrastructure. You don't need to write code, but you need to understand what's possible, what's expensive, and where technical constraints shape what you can build.

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $184,000/yr to $230,000/yr for New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for the New York office. Our open roles will specify on the careers page and in the job description where the position is eligible for work.

 ⁽¹⁾ Business Applications with Planned Wages (www.census.gov)

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees (1) 
• 550,000 new businesses are created each year in the US (1) 

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to come build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners - owning an entire roadmap end to end, and shaping the product from strategy setting through the nitty gritty execution details.
• Our Product team is lean, which means you’ll have a high degree of impact and ownership. 
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners. 

About the Team:

The Reporting team sits within the Core Experience organization and owns one of the most important experiences in the product: giving small business owners clear visibility into data about their payroll, benefits, and spend. 

We're at an inflection point. The back-end infrastructure that makes AI-native reporting possible  is taking shape and our next chapter is delivering those capabilities to customers in ways that are genuinely useful: fixing the basics, enabling AI-powered answers, and building a reporting experience that meets customers where they are. This PM will drive that work.

Here’s what you’ll do day-to-day:

• Drive the strategy and roadmap end-to-end. In close collaboration with your key partners in engineering, design and data, you'll set the strategic direction for Reporting and own the roadmap across all surfaces (web, mobile, and embedded experiences).
• Define the vision. You'll anchor the team and stakeholders around a clear, compelling vision for how traditional reports and AI-driven answers work together over time—one that connects to Gusto's broader AI transformation and gives everyone a coherent picture of where we're going.
• Ship customer-facing value every cycle. You'll hold yourself and the team accountable for delivering real improvements that customers notice and use, balancing fixing the basics and with bigger, future swings. 
• Partner with other product teams on real use cases. You'll work hand-in-hand with app teams like Pay and Benefits to deliver reporting capabilities end-to-end through real customer journeys, proving the infrastructure works and surfacing what needs to get better.
• Drive the data infrastructure forward. You'll bring rigor and clear prioritization to the ongoing data migration work, making sure back-end progress translates into customer-facing capability on a timeline that matters.
• Set up and track the right metrics. You'll define leading indicators for reporting quality and customer satisfaction, use data to drive continuous improvement, and communicate progress honestly to stakeholders.
• Raise the bar on collaboration. You'll work closely with engineering, design, and data partners to build a team that operates with speed and quality. You'll treat partner product teams as customers, giving them a clear path forward, answering their questions, and making it easy for them to build on what you've created.

Here’s what we're looking for:

• Customer obsession. You understand how small businesses use data to make decisions—questions they're actually trying to answer. You stay close to customers through direct research and indirect feedback loops (CX, support tickets, usage data), and you use what you learn to sharpen your priorities constantly. 
• Real AI fluency. You use AI tools in your own daily work for synthesis, ideation, analysis and prototyping ideas. You've built AI-powered product features or worked closely enough on them that you understand what good looks. You have a genuine point of view on what AI-native reporting means and where it's going. 
• Bias toward shipping. The Reporting team has strong foundations and the job now is to deliver. You set short, clear milestones. You move fast on near-term customer improvements while keeping the longer-term vision clear. You use staged rollouts and learning plans as a matter of course. You don't let platform work crowd out customer-facing progress because you hold both at once, and you know when to push and when to sequence. 
• Technical fluency in data. You're comfortable in conversations about data infrastructure: pipelines, data models, APIs, trade-offs between migration approaches. You don't need to write the SQL, but you understand what the engineers are building and why it matters for customers. You've worked on data products where back-end complexity is real and the front-end has to make it feel simple.
• Cross-functional partnership. Reporting sits at the intersection of almost every team at Gusto because  App teams depend on our platform to surface data to their customers. You treat partner teams as one of your most important customer groups—you understand their needs, you give them a clear path forward, and you make it easy to build on what you've created. 
• Clear, direct communication. You can tell a simple, compelling story about a complex system. You give stakeholders honest, specific progress updates. You escalate when something is off track and you come with a plan. You make it easy for people at any level to understand where Reporting is going and why it matters.
• Strategic clarity. You hold the near-term and long-term at the same time without letting one crowd out the other. You build a multi-year vision that connects to Gusto's AI transformation, and you sequence the work so that every cycle delivers meaningful customer value on the path to that vision. You know when to go narrow and when to open up scope, and you make that call quickly.

The experience we're looking for:

• 8+ years of hands-on product management experience
• At least some of that time spent on data products, analytics tools, reporting platforms, or infrastructure products where internal or external customers were a primary consideration
• Demonstrated track record of shipping customer-facing improvements at pace—things customers notice and use
• Experience with AI-powered product features or data experiences: building them, scoping them, evaluating them, or working closely enough on them that you understand the operational reality
• Strong cross-functional collaboration skills with engineering, design, and data partners
• Experience in environments where back-end platform maturity and front-end customer experience have to be balanced and advanced simultaneously

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is targeted at $180,000 to $224,000/yr in Denver & most major metro locations, and $210,000 to $263,000/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

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 3,000+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team: 

The Growth & Commerce team is responsible for the shared surfaces and platforms that power Gusto’s growth & primary revenue generating experiences. This includes being responsible for the acquisition flows, cross-sell & pricing experiences, as well as the infrastructure that powers pricing, invoicing and revenue communications. The team is responsible for a meaningful portion of Gusto’s overall revenue goals, and has central, shared responsibility for driving traffic to Gusto’s wide range of small business products. 

We are seeking a seasoned Product Manager with a creative mindset to join our New Customer Experience product team to manage the product experience and scalability for Gusto.com. This role will own the website roadmap, balancing improvements of the new customer experience on our signed out surfaces, and ensuring the website platform has long-term scalability and ecosystem health.

Here’s what you’ll do day-to-day: 

• Ownership: Own Gusto.com signed out product experience, ensuring potential new customers can quickly get the information they need to understand the relevant product offering. Uphold quality, performance, and accessibility standards across the ecosystem.
• North Star: Increase marketing experiment and campaign success with Gusto GTM team, and ensure healthy core web vitals across the Gusto.com stack.
• Partner with Growth to translate experiments into reusable system patterns.
• Partner with GTM to ship new campaigns for Gusto.com.
• Create scalable page patterns that balance brand, usability, and performance
• Define and evolve the website’s foundational design system (templates, layouts, components).
• Ensure visual and UX consistency across all web surfaces.
• Identify and reduce design debt while enabling faster GTM execution.

Here’s what we're looking for: 

• 5+ years of Product Management experience with a proven track record of shipping successful products
• Experience with using AI and automation in developing product solutions
• Understanding of small business challenges, with the ability to identify, frame, and articulate SMB pain points effectively
• Proven ability to work effectively across cross-functional teams including engineering, design, marketing, and sales
• Strong design partnership skills with the ability to collaborate with designers to push creative boundaries
• Excellent analytical and problem-solving capabilities with a data-informed approach to decision-making

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $184,000/yr to $230,000/yr for San Francisco. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for this role in San Francisco. Our open roles will specify on the careers page and in the job description where the position is eligible for work.  

 ⁽¹⁾ Business Applications with Planned Wages (www.census.gov)

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 3,000+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees (1) 
• 550,000 new businesses are created each year in the US (1) 

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners — owning an entire roadmap end to end and shipping product all the way from strategy through to the nitty-gritty details (some describe this kind of role as a “GM” type role).
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team:

The Tax Credits team is a “mini startup” within Gusto, and an incredibly talented group of people that have a mix of deep customer empathy, domain expertise, and a strong desire to innovate. Our mission is to grow and add value to our customer base, and continually test and refine tools designed to help these customers unlock savings through tax credits and grants. If you enjoy uncovering & solving big problems, driving lean experimentation, building 0 to 1 product experiences, and making a big impact on the lives of small business owners, we’d love to hear from you.

Here’s what you’ll do day-to-day:

• Ownership: Spearhead the development of a product & business aimed at unlocking value for existing Gusto customers as well as expanding Gusto’s customer base to new segments
• North Star: Unlocking savings for SMBs through tax credits
• Collaborate: Partner closely with Engineering, Design, Ops and Data Science on all stages of the product development process, and partner with the GM and Revenue team to grow the business and optimize its unit economics
• Lead product discovery to uncover and deeply understand customer problems and test risky assumptions
• Run lean experiments and A/B tests to quickly prove out hypotheses and test new concepts. Always looking for ways to get stronger signal on new ideas
• Create a long-term vision and strategy that defines the big problems we can solve well with a durable competitive advantage

Here’s what we're looking for:

• 8+ years of hands-on Product Management experience or 12+ years of relevant work experience
• Proven track record of building 0 to 1 products with nice to haves in:
• Strong product discovery skills and analytical skills
• The intangibles: natural curiosity, grit, customer obsession, and attention to detail
• The ability to tell a compelling story that drives alignment and inspires action
• Strong collaboration skills; ability to quickly build trust quickly
• A passion for helping small businesses

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $179,000/yr to $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team:

Gusto operates a scaled, full-suite benefits brokerage and is building a Professional Employer Organization (PEO) offering to serve more complex small businesses with a bundled solution for HR, payroll, benefits, and compliance. Our existing brokerage business is among the largest in the US serving the SMB market, and our PEO bet is one of our most strategic new initiatives, with FY26 focused on developing the foundation and FY27 aimed at launching a differentiated, scalable customer experience. 

We're looking for a Product Manager to lead the transformation of Gusto's benefits administration platform, the product that powers benefits for tens of thousands of SMBs and their employees. This role owns what happens after benefit selections are made: implementing plans with carriers, fulfilling enrollments, and giving customers visibility into the status of their benefits.  It is a broad scope, encompassing agentic workflows, customer-facing experiences, internal tooling, and carrier integrations.

Here’s what you’ll do day-to-day:

• Ownership: Lead long-term strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You’ll translate this strategy into actionable guidance that informs company-wide planning and execution.
• North Star: Focus the organization on what matters most. Identify the highest-leverage investments and decisions across functions that will unlock long-term success, reduce ambiguity, and ensure that Gusto is building toward a cohesive and differentiated Benefits & PEO offering.
• Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You’ll help create shared understanding and ensure cross-functional teams are set up to deliver.
• Accelerate Execution: Step into the highest-priority gaps that stand in the way of success. Whether it’s clarifying requirements, kicking off strategic initiatives, or embedding with a team to drive execution, you’ll help move the work forward by creating clarity, building momentum, and enabling others to succeed.

Here’s what we're looking for:

• 8+ years of product management experience, ideally with additional professional experience in roles that involved leading large, complex, and cross-functional initiatives
  • A systems thinker with experience in AI-driven workflows, operations platforms, and process transformation. Benefits experience is a plus, but not a requirement.
• Strong strategic thinking and the ability to connect work across customer needs, product design, internal operations, pricing, and go-to-market
• Excellent communication and storytelling skills, with a talent for making complexity understandable and actionable
• A bias towards action, comfort operating without a clear playbook, and a desire to drive meaningful progress on long-term company priorities

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $179,000/yr to $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. Our open roles will specify on the careers page and in the job description where the position is eligible for work. 

 ⁽¹⁾ Business Applications with Planned Wages (www.census.gov)

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team: 

We’re looking for a Senior Product Manager to lead Workflows for Gusto Pro, our product specifically built for Accountants. Accountants play a critical role within the Gusto ecosystem. They are one of our largest user groups, but also act as a one-to-many growth engine by referring their small business clients to use Gusto as their payroll provider, generating a substantial portion of our total revenue.

We have ambitious plans to become the most efficient platform for accountants to deliver payroll & advisory services to their clients and help millions of small businesses as a result. If you enjoy uncovering & solving big customer problems, making complex things simple, and identifying new ways to delight and disrupt workflows with AI, we’d love to hear from you.

Here’s what you’ll do day-to-day:

• Lead product discovery to uncover/deeply understand customer problems and test risky assumptions
• Create a long-term vision and strategy that defines the big problems we can solve well with durable competitive advantage
• Build iteratively to quickly prove out hypotheses and test new concepts, always looking for ways to get stronger signal on new ideas
• Partner closely with Engineering, Design, and Data Science on all stages of the product development process
• Rapidly execute and iterate with an emphasis on user delight, impact, and learning. Regularly take risks and make calculated tradeoffs
• Balance hands-on building with strategic storytelling that creates clarity and real value for the users we serve
• Define, measure, and improve key product and business metrics, especially in foundational areas like payroll task coordination, roles & permissions, reports, and other day-to-day workflows that are core to our users’ operations 

Here’s what we're looking for: 

• 5+ years of hands-on Product Management experience 
• Proven track record of leading R&D teams that deliver impactful results
• The intangibles: Natural curiosity, grit, customer obsession, and humility
• Strong product discovery and analytical skills
• The ability to tell a compelling story that drives alignment and inspires action
• Strong collaboration skills; ability to quickly build trust with teams and customers
• A passion for helping small and medium size businesses
• A strong POV on building products in the age of AI; experience building AI-driven features is a big bonus

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $184,000/yr to $230,000/yr for New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for the New York office. Our open roles will specify on the careers page and in the job description where the position is eligible for work. 

 ⁽¹⁾ Business Applications with Planned Wages (www.census.gov)

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to come build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners - owning an entire roadmap end to end and shipping product all the way from strategy through to the nitty gritty details (some describe this kind of role as a “GM” type role).
• Our Product team is lean, which means you’ll have a high degree of impact and ownership. 
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners. 

About the Role:

Gusto is in search of an exceptional product leader to oversee our Payroll product and business area on a global scale. Payroll is Gusto’s core product, used by each of our 400,000+ small business customers and contributing significantly to our annual recurring revenue. As a key member of Gusto’s product leadership team, you will assume end-to-end responsibility for the Payroll product strategy, roadmap, and business performance. You will directly lead the product team and indirectly oversee various cross-functional departments, all collaborating to deliver the ultimate Payroll experience for our valued customers. Your role will encompass building a dynamic team, a thriving business, and a suite of products that will be adored by our customers while setting industry benchmarks.

If you are a customer-centric builder who thrives on making a substantial impact within a high-growth organization, we would be thrilled to hear from you!

About the Team

Payroll is the heart of Gusto’s business, ensuring employees are paid accurately, on time, and in compliance with complex regulations. Our teams build and maintain the infrastructure and customer experiences that make payroll simple, reliable, and stress-free. We design user-friendly team management products that integrate seamlessly with Gusto’s broader Small Business Platform, combining digital solutions with human support where it’s needed most. We serve customers at every stage, from new employers hiring their first team members to growing businesses with expanding needs. No matter the size or complexity of your business, our solutions provide peace of mind and take the work out of paying your team.

Here’s what you’ll do day-to-day: 

• Ownership: Take ownership of the Payroll product and business area from end to end.
• North Star: Define and drive the long-term vision and strategy for Gusto Payroll, charting the future of how small businesses will pay and empower their teams, and positioning Payroll for its next era of growth and scale.
• Collaborate: Work with a strong cross-functional team of Engineers, Product Managers, Designers, and Data Scientists to bring your product strategy to life for customers.
• Empowerment: Directly coach and lead a talented team of senior product managers.

Here’s what we're looking for:

• 15+ years of hands-on product management experience across all roles/levels, with at least 5+ years leading and managing PMs (ideally teams of >=5).
• A people-first leader who builds, mentors, and empowers senior PMs, fosters an inclusive product culture, and inspires teams to deliver with clarity, ownership, and accountability.
• Background in SMB-focused software, with experience working in complex areas and regulated categories strongly preferred.
• Strong track record of building and scaling large, mission-critical products, with the ability to break down multi-year initiatives into pragmatic, high-impact launches.
• Skilled at collaborating across Engineering, Design, Data, Ops, Compliance, Finance, and GTM teams to drive adoption, revenue outcomes, and customer success.

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $206,000/yr to $248,000/yr in Denver & most major metro locations, and $243,000/yr to $292,000/yr for San Francisco, Seattle & New York. 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:

Are you looking for an opportunity to transform a business? Gusto is looking for a strategic, customer-focused leader to leverage customer feedback and operational key metrics to develop actionable insights and strategies that shape our product and service, and positively impact customer love.

Working with the Product, Engineering, Design and Customer Experience teams, you will be expected to tackle both highly strategic and deeply operational initiatives to deliver value for customers and Gusto. You’ll be customer-obsessed, business-minded, strategic, detail-oriented, and highly creative.

In this role, you'll help stand up the operational and service foundation for a new Gusto product, using both deep human judgment and emerging AI tools to move faster and make better decisions. If this sounds exciting to you, we’d love to connect!

About the Team:

The Benefits Product Operations team at Gusto is made up of committed, creative, collaborative people who care deeply about our mission to enable Benefits for all small and mid-sized businesses and their employees. We’re a highly cross-functional team focused on ensuring our product and service are co-designed and co-developed along the product lifecycle to deliver a best in class customer experience; Gusto is listening to, synthesizing and acting on customer and front-line team feedback; and that cross-functional teams are collaborating and swimming together to build the best version of Gusto for our customers.

Here’s what you’ll do day-to-day:

• Shape and support product development and its integration into service strategy for existing customers across the product lifecycle, in collaboration with Engineering, Design, Product Management, and Customer Experience teams.
• Understand our product and end-to-end service experience and organizations in intimate detail, including internal and external pain points and feedback.  Collaborate to ensure customer support considerations are integrated into broader company decisions.
• Lead and partner on product launches between Product Management and Customer Experience (CX) teams to ensure readiness and deliver insights post-launch to ensure a positive experience for customers and internal teams.
• Provide business insights and recommendations based on quantitative and qualitative data to influence strategy and operational design in both product and service roadmaps.
• Identify and drive cross-functional initiatives that will deliver value for customers and Gusto. Help develop and communicate a clear roadmap for enhancing service capabilities and experiences.
• Hypothesis-driven problem solving to drive our business.
• Contribute to advancing the Product Operations craft at Gusto and build AI fluency within the team:
  • Model how to use AI tools to accelerate service design, insight synthesis, and agent-driven operational workflows.
  • Identify and build AI-assisted operational workflows, including agents, to accelerate VoC synthesis, launch readiness monitoring, and cross-functional signal aggregation.
  • Use AI tools to prototype service solutions and surface requirements faster, compressing the feedback loop between customer signal and product/service response — before full engineering investment.

Here’s what we're looking for:

• 10+ years of relevant work experience at growing startups in operating roles (i.e., biz ops/strategy roles, product operations, project/program management, and/or consulting):
  • Experience scaling service strategy alongside growing SaaS products, including incubating products, building and managing product betas, and/or integrating new products into a scalable best-in-class service model.
  • Highly adaptable and resilient to changes in business needs or requirements, with the ability to navigate challenges and make decisions even when information is incomplete.
• Demonstrated self-starter and organized problem-solver. Self-sufficient, resourceful, and bias for action towards continuous improvement.
• Experienced with managing a variety of cross-functional stakeholders on complex strategic initiatives, including influencing senior leaders in Product or Customer Experience orgs.
• Strong data literacy and results-orientation, with the ability to identify the right questions, interpret quantitative and qualitative signals, and translate findings into decisions — including comfort using AI-assisted tools for analysis and synthesis.
• Excellent written and verbal communication skills, with the ability to effectively communicate complex subjects to both technical and non-technical audiences.
• Demonstrated AI fluency in an operational and product context — comfort using AI tools to synthesize qualitative data, identify automation opportunities in service workflows, and building or directing AI agents to reduce manual operational lift:
  • Experience prototyping with AI (e.g., Claude, Cursor, Codex or similar) is a plus.
• Experience with service design and/or service blueprinting.
• Experience working in the healthcare or benefits space (PEO, health insurance, etc.) is a plus; candidates with new product incubation experience in any complex regulated space are strongly encouraged to apply.

Our cash compensation amount for this role is $148,000/yr to $182,000/yr in Denver, and $167,000/yr to $217,000/yr 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.

By the Numbers:

• Named #1 best software for small business of 2024 by G2

About the Team:

Contractors is one of Gusto's fastest-growing business segments. The Contractor Products team owns end-to-end contractor management for SMBs—from onboarding to payments to compliance, across domestic and international contractors. With massive white space ahead, you'll have the chance to take products from 0→1 and beyond, solving real problems for hundreds of thousands of small businesses. We’re looking for someone with experience building 0→1 and able to own and drive growth levers for the contractors business.

Here’s what you’ll do day-to-day:

• Ownership: Lead long-term strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You’ll translate this strategy into actionable guidance that informs company-wide planning and execution.
• North Star: Build a long-term vision for how Gusto invests in contractor products—defining how we can simplify contractor management for SMBs and create durable competitive advantage
• Collaborate:  Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You’ll help create shared understanding and ensure cross-functional teams are set up to deliver.
• Make it happen. Be the pace setter. Drive execution as a boundaryless builder — doing whatever it takes to achieve outcomes. You will use AI as your co-builder to turn complex problems into durable, customer-loved solutions with urgency and care.

 Here’s what we're looking for:

• 5+ years of hands-on Product Management experience
• Proven track record of building 0-to-1 products—taking ideas from discovery through launch and iteration
• Strong customer discovery and product research skills with the ability to translate insights into actionable product strategies
• Solid data acumen with the ability to use data to inform decisions, set goals, and measure success
• Experience with AI tools and a vision for how AI can transform product experiences
• Exceptional cross-functional collaborator and leader—a great listener who naturally brings teams and stakeholders along, yet doesn't hesitate to make hard decisions when needed
• Ability to identify emerging opportunities, build business cases, define product vision, and create supporting roadmaps
• Entrepreneurial mindset, driven by our mission, with deep empathy for small business owners and their contractor workforce challenges
• A proven track record of building products that customers love

Our cash compensation amount for this role is $152,000/yr to $190,000/yr in Denver & most major metro locations, and $184,000/yr to $230,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Symmetry Software is part of Gusto. Symmetry is the payroll infrastructure for software & payroll platforms powering the paychecks of over 64 million workers each year. Our fully integrated suite of payroll tax APIs and software tools allows companies to solve tax compliance issues and build applications across the entirety of the payroll process.

What Product Management is like at Symmetry:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll pair sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing.
• We’re builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve the payroll industry. Our technology impacts over 64 million paychecks in the US each year. We’re driven by deep customer empathy and a relentless desire to innovate.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Symmetry.

About the Role:

We’re  looking for a product leader to own the development of new business lines for payroll tax products. This 0 to 1 focused role will have broad autonomy to lead discovery, strategy, and execution for new products in payroll tax. This role will be expected to deliver durable business outcomes such as new revenue and existing revenue retention.

The right person will be an activator who couples strength in execution with a strong sense of ownership to delivering market success. You will work directly with a new product development engineering team and focus on AI-powered solutions that redefine our market.

Here’s what you’ll do day-to-day:

• Ownership: Lead long-term strategy. This includes spearheading research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You’ll translate this strategy into actionable guidance that informs company-wide planning and execution.
• North Star: Focus the organization on what matters most. Identify the highest-leverage investments and decisions across functions that will unlock long-term success, reduce ambiguity, and ensure that Symmetry is building toward a market-winning payroll tax offering.
• Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You’ll help create shared context and ensure cross-functional teams are set up to deliver.
• Accelerate Execution: Step into the highest-priority gaps that stand in the way of success. Whether it’s clarifying requirements, kicking off strategic initiatives, or embedding with a team to drive execution, you’ll help advance the work by creating clarity, building momentum, and enabling others to succeed.

Here’s what we're looking for:

• 6+ years of hands-on product management experience, with 3+ years of success building 0 to 1 products
• Proven track record of building 0 to 1 products with demonstrable evidence of:
  • Deep product discovery skills with the ability to navigate a high degree of ambiguity
  • Building 0 to 1 products in highly regulated categories
  • Experience building personalized products or optimized workflows using Gen AI/ ML
  • Extraordinary cross-functional collaborator and leader
• Ability to identify emerging opportunities and industry trends, build business cases, define product vision and strategy, and create a supporting roadmap that rapidly iterates into delivering on your vision
• Entrepreneurial, passionate about our mission, and have deep empathy for our customers
• Built products at scale with good UX that users love
• Bonus points for experience with payroll / payroll tax

Compensation Details

Our cash compensation amount for this role is targeted at $143,000/yr to $179,000/yr in Scottsdale & most remote locations, and $184,000/yr to $230,000/yr for San Francisco & 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:

As the Founding Operations Leader at Gusto's broker-dealer entity, you will be the primary architect of our in-house carrying broker-dealer operations. You aren't here to follow a manual; you are here to write it. You will establish the operational objectives, policies, and work plans from the ground up, ensuring our AI-native infrastructure meets the highest standards of FINRA/SEC compliance and protect customers’ assets. You will report to and partner with the Head of Gusto's broker-dealer entity. You will build our operational blueprint serving as the bridge between customer impact,  technical innovation and regulatory rigor. You will design, oversee and execute essential back-office functions, focusing on the accurate movement of customer funds, transaction reconciliation and remediation, and reporting required for our broker-dealer entity. This role requires meticulous attention to detail, a commitment to process excellence and efficiency, and proven ability to lead and scale operational processes.

About the Team:

Gusto’s broker-dealer entity, a registered broker-dealer owned by Gusto Inc, forms the foundation for Gusto to expand our product offerings in retirement and investment. Gusto’s broker-dealer entity acts as the custodian of customers’ retirement assets and facilitates money movement and securities transactions, by integrating with the banking rails and clearing rails in the financial system. As a collaborative and technical group, we focus on designing, implementing, and monitoring the proprietary system and processes that meet the evolving demands of the retirement industry and regulatory landscape. You will join a team committed to building operational solutions that scale with Gusto’s mission to serve the small business economy.

Here’s what you’ll do day-to-day:

• Establish Operational Architecture: Author and implement the foundational operational objectives, policies, and procedures for our carrying broker-dealer. You will design the "0-to-1" work plans for money movement and trade clearing that will scale as we grow.
• Strategic Escalation & Decision Making: Serve as the final authority on operational exceptions. You will apply sophisticated judgment to resolve unusual circumstances where no precedent exists, understanding that your decisions directly impact Gusto’s results and long-term regulatory standing. Examples are complex stop-and-reissue checks, manual payment releases, ACH reversals, securities settlement breaks, net-capital calculation discrepancy),
• Controls & Audit Governance: Architect and maintain an operational control environment that meets the rigorous standards comparable to publicly traded companies. You will ensure that Gusto broker-dealer entity’s Internal Controls Over Compliance (ICOC) are robust, evidenced, and audit-ready by design for every customer transaction, setting a high bar for operational excellence. You will ensure that the transaction data produced is of the highest integrity, as it serves as a critical upstream feed into Gusto’s consolidated financial statements. You recognize that the quality of your team's work product directly affects our annual audits conducted by an independent PCAOB auditor, and has far-reaching implications to Gusto’s overall corporate governance.
• Cross-Functional Collaboration, Influence & Impact: Orchestrate complex partnerships with Engineering, Product, Legal, Compliance, FinOp, Accounting and FP&A to build Gusto’s  first-of-its-kind carrying broker-dealer. You are an expert at building consensus in sensitive regulatory environments, using data and operational insight to convince cross-functional stakeholders of the necessary balance between product innovation, execution velocity, uncompromising financial integrity and compliance requirements. You own the operational foundation that unlocks Gusto’s opportunities to expand our investment product offerings in 401(k), IRA and more diverse investment account types for Gusto’s member community to build wealth
• Fiscal Responsibility, Direction & Empowerment: Although you will start with building a small but mighty AI-native team, you’re responsible for establishing the team’s strategic direction, managing costs and demonstrating high ROI on the combination of headcount and AI agents. You’re also responsible for performance management and professional growth of the team, setting high bars for excellence and providing the coaching necessary to meet them.

Here’s what we're looking for:

• 10+ years of experience in a financial operations, treasury, or back-office role, with at least 5 years in a leadership or managerial capacity, preferably within a carrying broker-dealer or registered investment adviser environment.
• Required Licensing: FINRA SIE + Series 7 + Series 24.
• In-depth knowledge in SEC Rule 15c3-1 (Net Capital Rule), SEC Rule 15c3-3 (Customer Protection Rule), SEC Rule 17a-3 and 17a-4 (Recordkeeping Rule)
• In-depth  knowledge of cash and securities handling, settlement processes, and regulatory reporting requirements is a plus.
• Proven ability to perform and oversee complex reconciliations and transaction research.
• High degree of comfort working with analytical tools, banking technology systems, clearing technology systems, and  financial data/reporting systems.
• Exceptional organizational skills and meticulous attention to detail to manage and strategically improve daily, monthly, and quarterly operational cycles.
• Demonstrated ability to function at the Integrator level of AI fluency, consistently applying AI tools to complex analytical and operational tasks to drive efficiency and measurement accuracy
• Demonstrated ability to collaborate effectively with cross-functional stakeholders, external partners and regulators
• A Bachelor’s degree in Finance, Accounting, Business, or a related field.

Our cash compensation range for this role is $177,020 to $208,000 in New York, NY. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and amounts listed above.

About the Role:

At Gusto, we believe the next frontier of competitive advantage is the intelligence of the systems that power our people. As the Sr Principal PM, AI Workforce Enablement, you are the architect of the "Superhuman Agent." You won't just manage tools; you will redefine the relationship between Gusto’s workforce and technology. You are responsible for evolving our internal foundation into a proactive, agentic platform where AI handles the cognitive load, allowing our Go-to-Market (GTM) and Service teams to focus on high-value human connection. You will lead the transition of our legacy ecosystem into a future-state "exoskeleton" that empowers every employee to deliver an unparalleled, frictionless experience to our customers.

Gusto is looking for a hands-on builder to take on this leadership mantle as we rethink how people grow in an AI-native company. This role is not just about designing the systems that shape growth day-to-day, but the actual mechanics of work. You will be responsible for building new architecture and tearing down what no longer serves us. The goal is simple but hard: make growth obvious, continuous, and hard to avoid.

We’re looking for a leader who can balance strategic influence with hands-on craft—someone who can guide senior Gusto leaders through AI-native data strategy, coach data scientists on impactful problem solving, and dive in to drive forward statistically rigorous analyses when needed.

About the Team:

The Unified Service Platform (USP) product team serves as Gusto’s architectural backbone, responsible for engineering the intelligent, AI-driven ecosystem that brings GTM and Service operations into alignment. Our mission is to replace fragmented point solutions with a singular System of Intelligence—a digital exoskeleton that strips away administrative friction so our teams can focus on what matters most: our customers. Through our commitment to a #OneGusto experience, we provide the platform that ensures every internal interaction is backed by the full context of the customer journey.

We are an AI-native team building "agentic" solutions that transform how work happens. By mastering the AI-Human-AI loop, we own the delivery of a seamless, cross-channel journey across voice, chat, and email. Our goal is to ensure that our internal technical excellence creates an instant, easy and effortless experience for every business Gusto serves.

Here’s what you’ll do day-to-day:

• Architect of the "System of Intelligence": Lead the evolution of Gusto’s internal workspace by integrating 1P (first-party) and 3P (third-party) systems into a unified platform. Transform CRM into a proactive platform that anticipates agent needs and triggers automated workflows across the entire tech stack before manual intervention is required.
• Design the Future-State Agent Experience: Build the product mechanics for a symbiotic "AI-Human-AI" loop, where intelligent systems handle high-volume tasks and documentation, elevating our human experts to focus on high-value, high-empathy problem solving.
• Engineer the "Digital Exoskeleton": Ship real-time, context-aware assistance and agentic tools that eliminate cognitive load, enabling every Gustie to operate with "superhuman" speed and accuracy across voice, chat, and email.
• Lead with Technical Craft: Partner with Data Science and Engineering to bridge the gap between high-level AI strategy and rigorous execution, ensuring our models drive measurable gains in both agent productivity and employee sentiment.

Here’s what we're looking for:

• Visionary Product Leadership: 10+ years of experience in product management, with a proven track record of leading high-stakes internal platforms, RevOps, or Service technology at scale.
• AI Builder & Strategist: AI/ML specialist with deep expertise in LLMs and agentic workflows, building and shipping custom AI solutions that transform how teams work and scale.
• Systems Thinker: You see the "big picture" of how data and tools flow across a company and can architect solutions that solve for the end-to-end customer journey.
• Change Agent: Experience leading large-scale organizational transformations or merging complex technical teams into a unified organization.
• Human-Centric Empathy: A passion for "the work of work"—you are obsessed with making tools that employees love to use and that remove the friction from their daily lives.
• Strategic Execution: The ability to balance long-term 18-month missions (like #OneGusto) with the immediate tactical needs of a fast-growing GTM engine.

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $204,000/yr to $238,000/yr in Denver & most major metro locations, and $240,000/yr to $280,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾ 
• 550,000 new businesses are created each year in the US ⁽¹⁾ 

What Product Management is like at Gusto:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. 
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team: 

The Growth & Commerce team is responsible for the shared surfaces and platforms that power Gusto’s growth & primary revenue generating experiences. This includes being responsible for the acquisition flows, cross-sell & pricing experiences, as well as the infrastructure that powers pricing, invoicing and revenue communications. The team is responsible for a meaningful portion of Gusto’s overall revenue goals, and has central, shared responsibility for driving traffic to Gusto’s wide range of small business products. 

We are seeking a seasoned Product Manager with a creative mindset to drive growth through innovative customer onboarding strategies. This role involves developing an AI agent to escort the customer through Gusto’s complex onboarding experience. The ideal candidate will excel in creating AI experiences to help customers navigate the issues important to them. 

Here’s what you’ll do day-to-day: 

• Ownership: Own Gusto onboarding customer experiences related to driving conversion, especially experiences that assist customers navigate the complexities of Gusto payroll and expansion onboarding.
• North Star: Increase conversion of Gusto onboarding experience through experiences that simplify and clarify the overall and component specific onboarding process
• Collaborate: Tight collaboration will include the Gusto core experiences team, other growth teams and the various product teams associated with the onboarding - especially payroll, employee onboarding, state and federal tax registration

Here’s what we're looking for: 

• 8+ years of Product Management experience with a proven track record of shipping successful products
• Hands-on experience building and launching AI-powered customer experiences
• Vision for how AI can fundamentally transform digital experience design and user interaction paradigms
• Deep understanding of small business challenges, with the ability to identify, frame, and articulate SMB pain points effectively
• Demonstrated ability to craft compelling, action-oriented messaging that resonates with small business audiences
• Proven ability to work effectively across cross-functional teams including engineering, design, marketing, and sales
• Strong design partnership skills with the ability to collaborate with designers to push creative boundaries
• Excellent analytical and problem-solving capabilities with a data-informed approach to decision-making

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $179,000/yr to $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for this role in San Francisco. Our open roles will specify on the careers page and in the job description where the position is eligible for work.  

 ⁽¹⁾ Business Applications with Planned Wages (www.census.gov)

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing 
• Over $500M in annual revenue 
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs 
• There are 6.2M employers in the US, 98% have fewer than 100 employees (1) 
• 550,000 new businesses are created each year in the US (1) 

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to come build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners - owning an entire roadmap end to end, and shaping the product from strategy setting through the nitty gritty execution details.
• Our Product team is lean, which means you’ll have a high degree of impact and ownership. 
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners. 

About the Team:

Tax is a critical pillar of Gusto’s platform. The Tax Platform team owns the core systems that determine how tax liabilities are calculated, tracked, paid, reconciled, and filed for more than 400,000 small businesses.

These systems sit at the intersection of money movement, regulatory compliance, and customer trust. The Tax Platform provides shared capabilities used across Tax, Compliance, and R&D, shaping how tax data flows through the company and how other teams build safely on top of Gusto’s tax foundation.

This is high-leverage, system-level work. The team is actively modernizing tightly coupled legacy systems, improving correctness and traceability, and creating durable platform capabilities that reduce risk and unlock faster product development across the company. We partner closely with Engineering, Compliance, Legal, CX, Data Science, and Operations to ensure Gusto’s tax platform remains accurate, scalable, and resilient as the business grows.

Here’s what you’ll do day-to-day:

• Ownership: Own the strategy, roadmap, and execution for foundational Tax Platform systems, with responsibility for shaping platform direction across multiple quarters and years.
• North Star: Define and evolve a clear Tax Platform strategy that ladders into Gusto’s broader Tax strategy, bringing clarity to ambiguous problem spaces and guiding day-to-day decisions around prioritization, sequencing, and tradeoffs.
• Collaborate & Evangelize: Partner closely with Engineering, Compliance, Legal, CX, Data Science, and Product teams to align priorities, unblock dependencies, and drive adoption of shared platform capabilities. Translate between platform work and customer and business outcomes to help engineering teams understand impact and help stakeholders understand the value and tradeoffs of platform investments.
• Customer Impact: Tie platform initiatives to customer outcomes by using data, domain expertise, and partner input to prioritize work that improves accuracy, timeliness, trust, and operational reliability.
• Execution Excellence: Advocate for durable, correct, and scalable solutions while maintaining momentum through incremental delivery, thoughtful sequencing, and clear success metrics.

Here’s what we're looking for:

• 8+ years of product management experience, including meaningful ownership of platform teams, strategy and multi-year initiatives that created leverage across multiple teams or product areas.
• Demonstrated success operating in complex, multi-product environments with cross-team dependencies and internal platform customers.
• Strong system-level thinking and product judgment, with the ability to navigate ambiguity, make hard tradeoffs, and drive clarity without relying on consensus.
• Experience evolving or modernizing critical systems over time, balancing short-term delivery with long-term platform health and risk reduction.
• Comfort working in regulated or compliance-sensitive domains such as payroll tax, fintech, HR, or legal tech, with a deep appreciation for accuracy, auditability, and customer trust.
• Proven ability to partner closely with engineering teams and translate between platform decisions, customer impact, and business outcomes.
• A strong POV on building products in the age of AI; experience building AI-driven features is a big bonus

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is targeted at $180,000 to $224,000/yr in Denver & most major metro locations, and $210,000 to $263,000/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

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for the following Hubs: Toronto, Canada and Seattle, WA. Our open roles will specify on the careers page and in the job description where the position is eligible for work. 

 (1) Business Applications with Planned Wages (www.census.gov)