Principal Product Manager, Gusto
Gusto Solo
$210-263k
2-3 days a week in office
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
$210-263k
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 8+ years of hands-on Product Management experience
- Proven track record of building 0→1 products and scaling them into their next chapter of high growth
- You’re a builder at heart — entrepreneurial, curious, fluent, and stay up to date AI tools that help you move faster and think bigger. You’ve built or scaled AI-first products (whether at work or on your own) and see AI as a co-builder that expands what’s possible
- Experienced in building with modern AI systems — from prompting and fine-tuning to evaluating outputs and shipping reliable, user-facing experiences
- Experience building and scaling products in high growth startups and highly regulated domains (e.g., Fintech, Accounting, Taxes, Payroll) — you understand how to design systems that are both compliant and customer-obsessed
- GTM excellence — you’ve partnered with Marketing to craft promise→payoff, pricing/packaging, and lifecycle activation strategies that drive adoption and retention
- Exceptional collaboration and storytelling. You build trust quickly, drive alignment across teams, and communicate a compelling vision that inspires action
- 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
What the job involves
- 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
- As the Principal Product Manager, you’ll chart the course for Gusto Solo’s next phase of growth
- With the MVP now live, this role is about scaling — shaping the vision, deepening product-market fit, and unlocking new, AI-powered opportunities for solopreneurs
- You’ll collaborate closely with a fully staffed, high-performing cross-functional team that’s passionate about serving this customer base
- This is a critical role — your work will directly shape one of Gusto’s key growth drivers and define what an AI-first customer experience looks like for millions of small business owners
- Own the vision and strategy. Set the long-term direction for Gusto Solo — defining the big problems we can solve well and building toward durable competitive advantage. You’ll do this by continuously uncovering and deeply understanding customer needs, testing risky assumptions, running lean experiments, and staying close to trends and the market environment as the product evolves toward product–market fit
- Collaborate and influence. Partner across every function — Engineering, Design, Data Science, Service Delivery, Marketing, Finance, and more — to bring your bold vision to life. You’ll rally cross-functional teams and leaders around a shared strategy, building alignment and momentum to make that vision a reality
- Make it happen. Be the pace setter. Drive execution as a boundariless 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
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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