Principal Product Manager, AI Enabled Workforce

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. We have teams in Denver, San Francisco, and New York, supporting more than 400,000 small businesses across the country. We’re building a workplace that represents and celebrates the customers we serve. Total Rewards philosophy. 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 will redefine the relationship between Gusto’s workforce and technology. You will evolve 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 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 engage in 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 removes administrative friction so our teams can focus on what matters most: our customers. Through a #OneGusto experience, we provide a 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 Architect of the \"System of Intelligence\": Lead the evolution of Gusto’s 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 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 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. Here’s what we’re 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 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 work—making tools that employees love to use and remove friction from daily life. Strategic Execution: Ability to balance long-term missions with the immediate tactical needs of a fast-growing GTM engine. If you don’t think you meet all criteria but are interested, please apply. We’re looking for someone excited to join the team. Salary: $204,000 to $238,000 per year in Denver and major metro locations; $240,000 to $280,000 per year in San Francisco, Seattle, and New York. Final offer amounts vary by location, experience, and expertise. Working locations and equal opportunity Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees 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). Note: The San Francisco office expectations cover the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure internet connection is required. This includes non-office days for hybrid employees. We hire people from diverse backgrounds. Gusto is an equal opportunity employer. We do not discriminate in hiring or employment decisions based on race, color, religion, national origin, age, sex, pregnancy, marital status, ancestry, disability, veteran status, gender identity or expression, sexual orientation, or other protected characteristics. We provide reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you require an accommodation, please fill out this form and a team member will contact you. Gusto takes security of personal information seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected as part of your application will be subject to Gusto\'s Applicant Privacy Notice. #J-18808-Ljbffr Prudence Holdings