AI Operations Program Manager, Benefits

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 nationwide. The company has teams in Denver, San Francisco, and New York.

We are hiring an Operations Lead, internally named Labs Lead, to build and run Benefits Labs, the system that governs how Gusto's Benefits organization tests, validates, and scales operational change. This is an AI-native role: you will design and run the agents, automations, and workflows that power how work is triaged, how pilots are executed, and how evidence is generated and synthesized. You will own the full Labs lifecycle, including intake, pilot design, execution governance, measurement, and recommendations to leadership. This role reports to the Head of Benefits Business Operations.

• Operate and continuously improve the system that governs operational change across Benefits.
• Own intake and triage: run the AI-powered intake system that classifies, routes, and prepares incoming work.
• Run pilot governance: ensure every pilot follows a clear structure with defined success metrics, checkpoints, and outputs.
• Raise design quality: pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to standards.
• Build and improve the system: extend the existing agent and automation architecture across the Labs lifecycle.
• Solve systemic problems: convert repeatable problems into scalable, AI-powered workflows.
• Drive decision-making: develop analytical approaches and produce clear, evidence-based narratives.
• Lead cross-functional work: coordinate across product, engineering, operations, enablement, and business partners.
• Create clarity in ambiguity: lead discussions on complex operational and product topics.
• Produce leadership-ready outputs: deliver structured readouts, post-mortems, and recommendations using AI.
• Shape the future of Labs: inform the long-term operating model, team structure, and investment strategy.
• Raise the bar for others: coach Pilot Leads and BizOps partners on AI-powered ways of working.

• Proven ownership: delivered results end-to-end across complex, cross-functional work.
• AI-native builder (core requirement): designed and deployed AI agents, automations, or workflows that execute multi-step work, and measured the leverage created.
• Systems thinker: identify root causes at the process level and build solutions that scale.
• Strong data fluency: structure problems, define success metrics, and turn data into decision-driving narratives.
• Operator + coach: raise the quality of work around you through direct feedback, clear standards, and accountability.
• Cross-functional leader: led initiatives across product, engineering, and operations and drive alignment without direct authority.
• Comfort with ambiguity: create structure where none exists and move work forward without perfect information.
• Minimum experience: 4+ years in operations, program management, or business operations in a SaaS, technology, or operationally complex environment.
• Bonus: experience in benefits, insurance, or brokerage operations; experience with operational metrics; direct experience building or managing AI agents in a production or operational context.

Cash compensation: $98,725/year to $116,000/year in Denver & most major metro locations, and $114,285/year to $140,000/year for San Francisco & New York. All full-time employees receive competitive base pay, benefits, and equity (RSUs).

This role is based in Denver, CO and is Hybrid. Employees based in Denver, San Francisco, or New York City are expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).