AI Operations Program Manager, Benefits

About Gusto

At Gusto, were 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, en