Benefits Operations Lead

Denver, CO - Hybrid; Phoenix, AZ - Remote 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 executionand build systems that improve howthe business operates. Here’s what you’ll do day-to-day: You will operateand continuously improvethe system that governs operational change across Benefits.

• Own intakeand triage: Runthe AI-powered intake systemthat classifies,routes,and prepares incoming work.Determine theright path foreach requestand improve thesystem overtime.
• Run pilot governance: Ensure every pilot follows a clear structure with defined success metrics , checkpoints ,and outputs.Use AI-driven workflows to manage executionand produce recommendations to scale , iterate or stop.
• Raise design quality: Pressure-test hypotheses , refine success criteria,and hold Pilot Leads accountableto standards.Improve quality of work across system without taking ownership away from teams.
• Build & improve system: Extend existing agent & automation architecture across Labs lifecycle including intake routing workflow execution evidence synthesis readout generation; increase speed scope reliability over time.
• Solve systemic problems: Identify inefficiencies in operational change flow & convert repeatable problems into scalable AI-powered workflows.
• Drive decision-making: Develop analytical approaches & produce clear evidence-based narratives aligning stakeholders across product & CX influencing leadership decisions.
• Lead cross-functional work: Own coordination across product engineering operations enablement business partners; manage complexity align stakeholders deliver measurable outcomes.
• Create clarity in ambiguity: Lead discussions on complex operational/product topics helping teams converge on decisions/next steps.
• Produce leadership-ready outputs: Deliver structured readouts post-mortems recommendations using AI for efficient evidence generation/validation.
• Shape future of Labs: Use learnings/builds to inform long-term operating model team structure investment strategy for Benefits Labs.
• Raise bar for others: Coach Pilot Leads BizOps partners on AI-powered ways of working hold high standard for execution quality.

Here’s what we're looking for:

• Proven ownership: Owned outcomes across complex cross-functional work delivering results end-to-end.
• AI-native builder (core requirement): Designed/deployed AI agents automations workflows executing multi-step work; measured leverage created (required).
• Systems thinker: Identify root causes at process level build scalable solutions improving team operations beyond own output.
• Strong data fluency: Structure problems define success metrics turn data into clear decision-driving narratives.
• Operator + coach: Raise quality of work around through feedback clear standards accountability.
• Cross-functional leader: Led initiatives across product engineering operations driving alignment without direct authority.
• Comfort with ambiguity: Create structure where none exists move work forward without perfect info.

Minimum experience: 4+ years in operations program management or business operations in SaaS technology or operationally complex environment. Bonus: Experience in benefits insurance brokerage operations; working with operational metrics (cycle time quality throughput); direct experience building/managing AI agents in production/operational context. Additional Notes on Location & Work Arrangement: Gusto has physical offices in Denver San Francisco New York City; employees based there expected onsite ~2–3 days/week or more depending on role; same applies to subsidiary Symmetry office in Scottsdale AZ; San Francisco office expectations include San Jose metro area; remote work requires secure reliable consistent internet connection.