Senior Principal Product Manager, AI Enabled Workforce
About The Position
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.
Requirements
- 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 work"—you 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.
Responsibilities
- 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.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
Number of Employees
501-1,000 employees
