Senior Principal Product Manager at Gusto leading the design and architecture of an AI-native internal platform ("System of Intelligence") that integrates CRM, service operations, and agentic workflows. Role focuses on transforming how GTM and Service teams work through AI-human-AI loops and real-time assistance tools.
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 400,000 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 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:
Here’s what we're looking for:
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 $204,000,000/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.
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. This includes non-office days for hybrid employees.
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.
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