Principal Product Manager - Retirement

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.

• 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)

• 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.

Gusto Retirement helps small businesses offer cost-effective, easy-to-use retirement solutions so more people can build toward a secure retirement. We’re looking for a Principal Product Manager to lead growth initiatives across our Retirement product, driving adoption and engagement end-to-end. You’ll set strategy and priorities, run experiments, and ship improvements from ideation through execution to accelerate growth across key funnels (employer setup, employee enrollment, and ongoing contributions).

You’ll also explore new product opportunities/JTBD that expand how we serve SMBs and unlock new avenues for growth.

• Ownership:
  Lead growth initiatives across Gusto Retirement, owning key funnels and levers that increase adoption, engagement, and retention for SMBs and their employees.
• North Star:
  Set a long-term growth vision and strategy. Define the biggest problems to solve, where we can win, and the roadmap of bets to get there.
• Explore new opportunities:
  Identify new product opportunities/JTBD (new surfaces, features, or offerings) that unlock step-function growth and expand who we serve.
• Collaborate and influence:
  Partner closely with Engineering, Design, Data, Ops/Compliance, Legal, Marketing, Finance, and more to align on strategy, make smart tradeoffs, and deliver results.
• Measurement:
  Define KPIs, baselines, and instrumentation; run rigorous experiments and reviews to ensure we’re improving customer outcomes and business health.
• Make it happen:
  Be the pace setter. Drive execution with urgency and high standards, unblocking the team however needed. Use AI as a co-builder to move faster from insight → iteration → durable, customer-loved solutions.

• 8+ years of product management experience in B2B SaaS or the Fintech/Regtech space
• Experience building and scaling products in high growth startups and highly regulated domains
• Excellent analytical skills with the ability to translate complex business problems into clear, concise product requirements.
• Proficiency in SQL
• Curiosity and a passion for fintech and financial products
• Comfor…