AI Operations Program Manager, Benefits

Gusto's mission is to grow the small business economy by handling payroll, health insurance, 401(k)s, and HR for small businesses. With teams in Denver, San Francisco, and New York, they support more than 500,000 small businesses nationwide. All full-time employees receive competitive base pay, benefits, and equity (RSUs).

We're 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. The goal is to create a system that can run many pilots in parallel with high quality and minimal manual intervention.

• 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, including intake routing, workflow execution, evidence synthesis, and readout generation.
• Solve systemic problems: Identify inefficiencies and convert repeatable problems into scalable, AI-powered workflows.
• Drive decision-making: Develop analytical approaches and produce clear, evidence-based narratives that align stakeholders across product and CX.
• Lead cross-functional work: Own coordination across product, engineering, operations, enablement, and business partners.
• 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: You've owned outcomes across complex, cross-functional work and consistently delivered results end-to-end.
• AI-native builder (core requirement): You've designed and deployed AI agents, automations, or workflows that execute multi-step work, and you've measured the leverage created.
• Systems thinker: You identify root causes at the process level and build solutions that scale.
• Strong data fluency: You can structure problems, define success metrics, and turn data into clear, decision-driving narratives.
• Operator + coach: You raise the quality of work around you through direct feedback, clear standards, and accountability.
• Cross-functional leader: You've led initiatives across product, engineering, and operations and can drive alignment without direct authority.
• Comfort with ambiguity: You 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 working 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).

Apply via the Gusto Greenhouse job board link.