Gusto, Inc.: Benefits Operations Lead
Headquarters: 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). 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.
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. Labs sits across these domains as the governance layer for operational change, ensuring ideas are tested rigorously, measured consistently, and scaled intentionally.
Responsibilities
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.
- Run pilot governance: Ensure every pilot follows a clear structure with defined success metrics, checkpoints, and outputs.
- Raise design quality: Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to standards.
- Build and improve the system: Extend the existing agent and automation architecture across the Labs lifecycle.
- Solve systemic problems: Identify inefficiencies and convert repeatable problems into scalable, AI-powered workflows.
- Drive decision-making: Develop analytical approaches and produce clear, evidence-based narratives to influence leadership.
- 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.
- 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.
- Raise the bar for others: Coach Pilot Leads and BizOps partners on AI-powered ways of working.
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 have designed and deployed AI agents, automations, or workflows that execute multi-step work and have measured the leverage created.
- 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 experience: 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 (e.g., cycle time, quality, throughput); direct experience building or managing AI agents in a production or operational context.
Compensation
- Denver & most major metro locations: $98,725 – $116,000/year
- San Francisco & New York: $114,285 – $140,000/year Final offer amounts are determined by multiple factors including candidate location, experience, and expertise.
Office Expectations
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days approximately 2-3 days per week. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.
Equal Opportunity
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. If you require a medical or religious accommodation, please fill out this form.
Additional Information
To apply: https://weworkremotely.com/remote-jobs/gusto-inc-benefits-operations-lead