Senior Product Manager, Payroll Engine (Chicago)

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About Gusto
Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

About Gusto
Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.
Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. Thats why were committed to building a collaborative and inclusive workplace, both physically and virtually. 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 (1)
• 550,000 new businesses are created each year in the US (1)
  

What Product Management Is Like At Gusto

• Were 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 youll have a high degree of impact and ownership.
• Were 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
Payroll is the beating heart of Gusto. The Payroll Engine team owns the systems that calculate every paycheck and orchestrate the workflows that power tax calculation, payments, filings, and compliance for over 400,000 small businesses across the country.
The Payroll Engine team owns the core platforms that every payroll run depends on. It drives how earnings are calculated, how data flows between systems, and how internal teams build, scale, and innovate on top of payroll. The platform processes billions of dollars in payroll each month and plays a foundational role in the new products Gusto brings to market.
This is deeply technical, high-leverage work. The team focuses on strengthening system extensibility, improving observability, and enabling every other team at Gusto to move faster with greater reliability and flexibility. We collaborate closely with Engineering, Design, Compliance, Legal, CX, Data Science, and Operations to ensure our systems meet the needs of both customers and internal developerstoday and into the future.
Heres What Youll Do Day-to-day

• Ownership: Lead the strategy, roadmap, and execution for the core systems that power every payroll run at Gusto. Drive platform improvements in extensibility, observability, and developer experience to help internal teams build faster and with greater confidence.
• North Star: Bring clarity to complex, ambiguous problem spaces by identifying the most critical opportunities for impact. Use customer outcomes, business goals, and technical realities to guide prioritization and ensure the team is always focused on what matters most.
• Collaborate & Evangelize: Work closely with Engineering, Compliance, Design, Data Science, CX, Legal, and Operations to tackle complex, high-stakes problems in a regulated domain.Champion platform adoption by ensuring the Payroll Engine is intuitive, flexible, and easy to build on.
• Customer Impact: Tie platform investments to customer outcomes by using data, partner input, and business context to prioritize work that improves accuracy, timeliness, and trust.
• Execution Excellence: Advocate for long-term quality, scalability, and flexibility while maintaining a strong focus on delivering impact through thoughtful execution.
  

Heres What We're Looking For

• 5+ years of product management experience, including meaningful ownership of platform or infrastructure systems in technically complex environments.
• Proven track record of shipping high-scale, backend or platform products with real business and customer impact.
• Strong systems thinking and product craft, with the ability to navigate ambiguity, influence without authority, and drive clarity across engineering and cross-functional teams.
• Experience developing multi-year strategies, balancing flexibility and stability, and modernizing critical systems in a way that enables broader product innovation.
• Comfort working in regulated or compliance-sensitive domains such as fintech, payroll, HR, or legal tech, with a deep appreciation for trust, accuracy, and risk reduction.
  

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 $152,000 to $190,000/yr in Denver & most major metro locations, and $184,000 to $230,000/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 Centers of Gravity: Toronto, Canada, Atlanta, GA, Austin, TX, Chicago, IL, Denver, CO, Los Angeles, CA, Miami, FL, and Seattle, WA. Our open roles will specify on the careers page and in the job description where the position is eligible for work.

• Business Applications with Planned Wages (

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.
Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.
When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Product Management and Marketing

• Industries

  Software Development

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