AI Operations Program Manager, Benefits

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy . AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. 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 is not a traditional program or operations role. Your responsibility is to build and operate the system that runs Labs. 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. The goal is to create a system that can run many pilots in parallel with high quality and minimal manual intervention. Your impact is measured by leverage: how much work the system can handle without you, how quickly the organization can test and scale changes, and how clearly leadership can make decisions based on evidence. Benefits Labs sits within Benefits Business Operations today. You will be the founding operator, reporting to the Head of Benefits Business Operations, and will directly shape how this function evolves, including its future scope, structure, and investment. About the Team: Benefits Business Operations is responsible for how Gusto’s Benefits business improves and scales. The team operates across three domains: Automation, Carrier, and Quality, each focused on improving different parts of the operational system. Labs sits across these domains as the governance layer for operational change. It ensures ideas are tested rigorously, measured consistently, and scaled intentionally. Labs partners closely with org leadership, product, engineering, and transformation teams to turn strategy into execution and build systems that improve how the business operates. Here’s what you’ll do day-to-day: You will 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. Determine the right path for each request and improve the system over time. • Run pilot governance: Ensure every pilot follows a clear structure with defined success metrics, checkpoints, and outputs. Use AI-driven workflows to manage execution and produce recommendations to scale, iterate, or stop. • Raise design quality: Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to standards. Improve the quality of work across the system without taking ownership away from teams. • 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. Increase speed, scope, and reliability ov