Senior Principal Product Manager, AI Enabled Workforce

About Gusto

At Gusto were 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 400000 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 wont just manage tools; you will redefine the relationship between Gustos 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.

Were looking for a leader who can balance strategic influence with hands-on craftsomeone 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 Gustos 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 Intelligencea 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.

Heres what youll do day-to-day:

• Architect of the System of Intelligence: Lead the evolution of Gustos internal workspace by integrating 1P (first-party) and 3P (third-party) systems into a unified platform. Transform CRM into a proactive platform that anticipates agent needs and triggers automated workflows across the entire tech stack before manual intervention is required.
• Design the Future-State Agent Experience: Build the product mechanics for a symbiotic AI-Human-AI loop where intelligent systems handle high-volume tasks and documentation elevating our human experts to focus on high-value high-empathy problem solving.
• Engineer the Digital Exoskeleton: Ship real-time context-aware assistance and agentic tools that eliminate cognitive load enabling every Gustie to operate with superhuman speed and accuracy across voice chat and email.
• Lead with Technical Craft: Partner with Data Science and Engineering to bridge the gap between high-level AI strategy and rigorous execution ensuring our models drive measurable gains in both agent productivity and employee sentiment.

Heres what were looking for:

• Visionary Product Leadership: 10 years of experience in product management with a proven track record of leading high-stakes internal platforms RevOps or Service technology at scale.
• AI Builder & Strategist: AI/ML specialist with deep expertise in LLMs and agentic workflows building and shipping custom AI solutions that transform how teams work and scale.
• Systems Thinker: You see the big picture of how data and tools flow across a company and can architect solutions that solve for the end-to-end customer journey.
• Change Agent: Experience leading large-scale organizational transformations or merging complex technical teams into a unified organization.
• Human-Centric Empathy: A passion for the work of workyou are obsessed with making tools that employees love to use and that remove the friction from their daily lives.
• Strategic Execution: The ability to balance long-term 18-month missions (like #OneGusto) with the immediate tactical needs of a fast-growing GTM engine.

If you dont think you meet all of the criteria above but still are interested in the job please apply. Nobody checks every box and were looking for someone excited to join the team.

Our cash compensation amount for this role is $/yr to $238000/yr in Denver & most major metro locations and $240000/yr to $280000/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 Gustos 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 its 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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