AI Operations Program Manager, Benefits

About the Role

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.

You will own the full Labs lifecycle, including intake, pilot design, execution governance, measurement, and recommendations to leadership. This role is AI-native: 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.

Responsibilities

• 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 in operational change workflows and convert repeatable problems into scalable, AI-powered workflows.
• Drive decision-making: Develop analytical approaches and produce clear, evidence-based narratives to align stakeholders across product and CX.
• 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, helping teams converge on decisions.
• Produce leadership-ready outputs: Deliver structured readouts, post-mortems, and recommendations using AI to generate and validate evidence.
• Shape the future of Labs: Inform the long-term operating model, team structure, and investment strategy for Benefits Labs.
• Raise the bar for others: Coach Pilot Leads and BizOps partners on AI-powered ways of working.

Qualifications

Minimum Qualifications

• 4+ years of experience in operations, program management, or business operations in a SaaS, technology, or operationally complex environment.
• AI-native builder (core requirement): Proven experience designing and deploying AI agents, automations, or workflows that execute multi-step work, with measured leverage created.
• Proven ownership across complex, cross-functional initiatives.
• Strong systems thinking and data fluency.
• Experience leading and aligning cross-functional teams across product, engineering, and operations.

Preferred Qualifications

• Experience in benefits, insurance, or brokerage operations.
• Experience working with operational metrics (e.g., cycle time, quality, throughput).
• Direct experience building or managing AI agents in a production or operational context.