Senior 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 — 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: 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 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. 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 archite