AI Operations Program Manager, Benefits

Gusto, Inc.•Denver, CO

2d•$98,725 - $140,000

About The Position

Gusto is hiring an Operations Lead, internally named Labs Lead, to build and run Benefits Labs, the system governing how the Benefits organization tests, validates, and scales operational change. The role owns the full Labs lifecycle, including intake, pilot design, execution governance, measurement, and recommendations to leadership. It focuses on building and operating the system that runs Labs rather than serving as a traditional program or operations role. This is an AI-native role. The Labs Lead will design and run agents, automations, and workflows to triage work, execute pilots, and generate and synthesize evidence. The goal is to enable many pilots to run in parallel with high quality and minimal manual intervention. Success is measured by the leverage the system creates, the speed at which the organization can test and scale changes, and the clarity of evidence available to leadership. Benefits Labs sits within Benefits Business Operations, and the founding operator reports to the Head of Benefits Business Operations. The role will help shape the function’s future scope, structure, and investment. Labs operates across Automation, Carrier, and Quality, partnering with organizational leadership, product, engineering, and transformation teams to turn strategy into execution and improve business operations. The position requires ownership of complex cross-functional work, strong data fluency, systems thinking, and the ability to build and deploy AI agents, automations, or workflows that execute multi-step work. The role also coaches Pilot Leads and Business Operations partners, drives alignment without direct authority, and creates structure amid ambiguity. Gusto has offices in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days approximately two to three days per week, or more depending on the role. When approved to work elsewhere, employees need a secure, reliable, and consistent internet connection. Regular and predictable attendance is expected for in-office, hybrid, and remote employees.

Requirements

At least 4 years of experience in operations, program management, or business operations in a SaaS, technology, or operationally complex environment.
Demonstrated ownership of outcomes across complex, cross-functional work and consistent end-to-end delivery.
Experience designing and deploying AI agents, automations, or workflows that execute multi-step work, and measuring the leverage created; this is a core requirement.
Ability to identify process-level root causes and build scalable solutions that improve how teams operate.
Strong data fluency, including structuring problems, defining success metrics, and turning data into clear, decision-driving narratives.
Ability to raise the quality of others’ work through direct feedback, clear standards, and accountability.
Experience leading initiatives across product, engineering, and operations and driving alignment without direct authority.
Ability to create structure and move work forward amid ambiguity.

Nice To Haves

Experience in benefits, insurance, or brokerage operations.
Experience working with operational metrics such as cycle time, quality, and throughput.
Direct experience building or managing AI agents in a production or operational context.

Responsibilities

Own and continuously improve the system that governs operational change across Benefits.
Run the AI-powered intake system to classify, route, and prepare incoming work; determine the appropriate path for requests and improve the system over time.
Govern pilots by ensuring each has a clear structure, success metrics, checkpoints, and outputs; use AI-driven workflows to manage execution and recommend whether to scale, iterate, or stop.
Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to standards while improving work quality without taking ownership away from teams.
Extend the agent and automation architecture across the Labs lifecycle, including intake routing, workflow execution, evidence synthesis, and readout generation.
Identify systemic inefficiencies in how operational change moves through the organization and turn repeatable problems into scalable, AI-powered workflows.
Develop analytical approaches and evidence-based narratives that align stakeholders across product and customer experience and influence leadership decisions.
Coordinate cross-functional work across product, engineering, operations, enablement, and business partners; manage complexity, align stakeholders, and deliver measurable outcomes.
Lead discussions on complex operational and product topics to help teams reach decisions and agree on next steps.
Produce structured leadership readouts, post-mortems, and recommendations, using AI to generate and validate evidence efficiently.
Use lessons from the work to inform the long-term operating model, team structure, and investment strategy for Benefits Labs.
Coach Pilot Leads and Business Operations partners on AI-powered ways of working and uphold a high standard for execution quality.