Senior Product Manager, Tax Payments and Filing

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About Gusto 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. 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 • 550,000 new businesses are created each year in the US 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 Role: Every employer has to pay and file its taxes correctly and on time: to the right agency, the right form, the right day. At Gusto, our Tax Payments & Filings team owns that promise for more than 500,000 businesses and millions of employees, moving billions of dollars to federal, state, and local agencies. You'll join the team building the tooling, automation, and AI-enabled systems that keep Gusto ahead of constant regulatory change, working shoulder-to-shoulder with the Operations and Compliance teams who are your primary customers and the engineers who know this domain deeply. It's high-leverage, deeply technical product work at the core of what makes Gusto trustworthy. About the Team: • Ownership: Own the investment strategy for how Gusto gains leverage over tax compliance. Decide where the team places its bets, which capabilities to build, and how to sequence them for the biggest return, and set the long-term direction for where tax compliance at Gusto is headed. You'll make the hard tradeoffs about where we spend our time and resources and turn them into a clear plan the team can execute against. • North Star: Compliance that scales faster than Gusto grows: every customer's taxes handled correctly and on time, no matter how fast the rules change or how much volume we add, • Collaborate: Partner across Engineering, Design, Operations, Compliance, Legal, and CX to find where the real friction is, validate solutions, and build alignment. Your primary customers are internal, the Operations and Compliance teams, and your job is to make them dramatically more effective. • Make it happen. You're here to build, hand in hand with your team. You'll prototype, get into the weeds of tax, and use AI to ship scalable solutions faster than the rules can change. You'll turn the real complexity of tax into systems that just work, and you'll own the outcome end to end. Here’s what we're looking for: • 5+ years of hands-on product management experience, including ownership of internal-facing platforms, tooling, or operational systems. • A track record of driving leverage: building automation, tooling, or system improvements that removed real work. • Strong technical fluency and a genuine partnership with engineering, with comfort operating in complex codebases. • Experience in a compliance-driven or highly regulated domain, where correctness isn't optional and a government agency or regulator is effectively a stakeholder (ex. financial services, banking, insurance, tax, healthcare, or benefits). • Hands-on experience with AI and automation. • You use data to find the highest-leverage opportunities, set goals, and measure impact. • An exceptional cross-functional partner, especially with internal customers like Operations and Compliance and with engineering. • Ability to bring structure to ambiguity: define direction, sequence the work, and make deliberate prioritization tradeoffs based on clear frameworks. 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