AI Operations Program Manager, Benefits

Skills this role screens for

About the role

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.

The work

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.

The company

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.

The work

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 over time.
• Solve systemic problems: Identify inefficiencies in how operational change moves through the organization and convert repeatable problems into scalable, AI-powered workflows.
• Drive decision-making: Develop analytical approaches and produce clear, evidence-based narratives that align stakeholders across product and CX and influence leadership decisions.
• Lead cross-functional work: Own coordination across product, engineering, operations, enablement, and business partners. Manage complexity, align stakeholders, and deliver measurable outcomes.
• Create clarity in ambiguity: Lead discussions on complex operational and product topics, helping teams converge on decisions and next steps.
• Produce leadership-ready outputs: Deliver structured readouts, post-mortems, and recommendations using AI to generate and validate evidence efficiently.
• Shape the future of Labs: Use what you build and learn to 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 and hold a high standard for execution quality.

Who they want

Here’s what we're looking for

• Proven ownership: You’ve owned outcomes across complex, cross-functional work and consistently delivered results end-to-end.
• AI-native builder (core requirement): You don’t just use AI tools. You build with them. You’ve designed and deployed AI agents, automations, or workflows that execute multi-step work, and you’ve 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. You improve how teams operate, not just your own output.
• 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.

Who they want

Minimum experience

4+ years in operations, program management, or business operations in a SaaS, technology, or operationally complex environment.

Nice to have

Bonus

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.

Our cash compensation amount for this role is $98,725/year to $116,000/year in Denver & most major metro locations, and $114,285/year to $140,000/year for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.…