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Salary: USD 98,725 - 116,000 / annual
Gusto is hiring an AI Operations Program Manager (internally titled Labs Lead) to build and operate Benefits Labs, the governance system for how Gusto's Benefits organization tests, validates, and scales operational change. This is a founding operator role reporting to the Head of Benefits Business Operations.
You will own the complete Labs lifecycle: intake, pilot design, execution governance, measurement, and leadership recommendations. This is not a traditional program role—your core responsibility is designing and operating an AI-native system that runs operational pilots with minimal manual intervention.
Key responsibilities:
- Operate and continuously improve the system governing operational change across Benefits
- Own intake and triage: Run the AI-powered intake system that classifies, routes, and prepares incoming work; refine the system over time
- Run pilot governance: Ensure every pilot has defined success metrics, checkpoints, and outputs; use AI-driven workflows to manage execution and produce scaling recommendations
- Raise design quality: Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to high standards
- Build and improve the system: Extend the existing agent and automation architecture across the Labs lifecycle (intake routing, workflow execution, evidence synthesis, readout generation); increase speed, scope, and reliability
- Solve systemic problems: Identify inefficiencies and convert repeatable problems into scalable, AI-powered workflows
- Drive decision-making: Develop analytical approaches and produce evidence-based narratives that influence leadership decisions
- Lead cross-functional work: Own coordination across product, engineering, operations, enablement, and business partners
- Create clarity in ambiguity: Lead discussions on complex operational and product topics to drive convergence
- 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
- Coach and raise the bar: Mentor Pilot Leads and BizOps partners on AI-powered ways of working
Your impact is measured by leverage: how much work the system handles without you, how quickly the organization can test and scale changes, and how clearly leadership can make decisions based on evidence.
Benefits Business Operations is responsible for improving and scaling Gusto's Benefits business across three domains: Automation, Carrier, and Quality. Labs sits across these domains as the governance layer, partnering closely with org leadership, product, engineering, and transformation teams.
Gusto is on a mission to grow the small business economy by handling payroll, health insurance, 401(k)s, and HR. The company supports more than 500,000 small businesses nationwide with teams in Denver, San Francisco, and New York. All full-time employees receive competitive base pay, benefits, and equity (RSUs). AI is a fundamental part of how work gets done at Gusto, and all team members are expected to actively engage with AI tools relevant to their role.
Requirements:
- 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 measured the leverage created. This is required for success in this role
- 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 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 (cycle time, quality, throughput); direct experience building or managing AI agents in production or operational context
