Principal Product Manager

Gusto is on a mission to grow the small business economy, handling payroll, health insurance, 401(k)s, and HR for over 500,000 small businesses. With teams in Denver, San Francisco, and New York, Gusto is building an AI-first workplace where all team members are expected to engage with AI tools relevant to their role.

As Principal Product Manager for the AI-First Service Platform, you will own core capabilities of the intelligence layer and surface area experience behind Gusto's customer-facing AI help/service. You will own multiple capabilities and/or channels across voice, chat, and email, and be accountable for system performance for customers.

• Own core capabilities of Gusto's AI service intelligence layer (e.g., intent understanding, escalation and handoff decisions, context ingestion, knowledge and retrieval) across voice, chat, and/or email.
• Build and refine models and frameworks that decode customer needs and determine whether AI or a human is the right path to resolution, partnering with engineering and data science.
• Own the evaluation layer for shipped systems—define what 'good' means, build evals and monitoring, and close the loop between model behavior and customer experience.
• Experiment, learn, iterate, and ship impactful solutions rapidly.
• Identify and dismantle legacy systems and hard-coded workflows, replacing them with flexible, intelligent architecture.
• Collaborate with GTM and Service teams to reflect real operational needs and translate frontline insights into prioritized product decisions.
• Define and track metrics—solve rate, satisfaction, escalation accuracy, handle time, and customer effort—to drive continuous improvement.

• 8+ years of product management experience building complex, data-intensive platforms—ideally in customer service, CRM, or enterprise SaaS environments.
• Deep familiarity with AI/ML concepts—particularly intent classification, NLP, and agentic systems—with a track record of translating model capabilities into product outcomes at scale.
• A hands-on builder who can move fluidly between strategy and execution, comfortable whiteboarding architecture with engineers and influencing senior stakeholders.
• Strong cross-functional instincts and ability to align Sales, Service, and Engineering teams around a shared product vision.
• A bias toward simplicity, defaulting to first principles and measuring success by friction removed.

Cash compensation is $179,000/yr to $220,000/yr in Denver & most major metro locations, and $210,000/yr to $260,000/yr for San Francisco, Seattle & New York. All full-time employees receive competitive base pay, benefits, and equity (RSUs).

Hybrid - Denver, CO; New York, NY; San Francisco, CA. Employees based in those locations are expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).

Apply via the Gusto Greenhouse job board at the provided URL.