Job Description
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 500000 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 a Strategic 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 execution and build systems that improve how the business operates.
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.
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.
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.
Our cash compensation amount for this role is $98725/year to $116000/year in Denver & most major metro locations and $114285/year to $140000/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.
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.
When approved to work from a location other than a Gusto office a secure reliable and consistent internet connection is required. This includes non-office days for hybrid employees.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because it's the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.
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 (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
Skills Required
- Proven ownership across complex cross-functional work
- 4+ years in operations program management or business operations
- Experience in benefits insurance or brokerage operations
- Direct experience building or managing AI agents
What the Team is Saying
Gusto Compensation & Benefits Highlights
- Healthcare Strength—Medical dental and vision coverage is described as comprehensive for employees and dependents with mental‑health resources included. Health benefits are also available and administered within one system that syncs with payroll.
- Inclusive Benefits Coverage—Family planning and fertility support gender‑affirming care and a range of mental‑health resources extend coverage to diverse needs. Adoption assistance childcare benefits and return‑to‑work support further broaden inclusivity for different family structures.
- Leave & Time Off Breadth—Paid vacation sick time bereavement holidays and paid leaves form a wide time‑off foundation. A sabbatical program adds longer‑term rest options beyond standard PTO.
Gusto Insights
What We Do
Gusto is a modern online small business platform that helps small businesses take care of their teams. On top of full-service payroll Gusto offers health insurance 401(k)s expert HR and team management tools. Today Gusto offices in Denver San Francisco and New York serve more than 400000 businesses. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because it's the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.
Why Work With Us
We help small businesses—the backbone of the economy—thrive. Everything we do ladders up to empowering entrepreneurs and supporting their teams. Gusto empowers builders at every level to take initiative and make things better. You'll be solving meaningful challenges that shape the future of work.
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Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We’ve built an inclusive connected culture—no matter where you live. Whether near an office or remote you’ll find opportunities to connect grow and belong. Employees work from the office on 2 designated days per week.
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Date Posted
05/21/2026
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