Similar Jobs at Gusto
About Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.
About the Role:
As an Insights & Operations (I&O) Partner in the Pay Group, you will play a critical role in helping Gusto deliver on its vision of making the work of paying your team disappear. The Pay Group is the last doorway to financial stability and peace of mind for small business owners and their teams.
You’ll primarily partner with leaders in the Tax domain, whose job is to make tax compliance feel invisible—ensuring withholding, payments, and filings are accurate and on time. You will also collaborate with Payroll, Time, and Contractors + Employer of Record teams as the role expands.
This role blends strategic program management and business operations / chief of staff support. You’ll be the first call when senior leaders hit ambiguity, when cross-functional programs need lift-off, or when a critical initiative risks stalling.
About the Team:
The Pay Group builds core products and services that power Gusto’s platform:
- Tax – Withholding, accounts, payments, and filings that earn customer trust.
- Payroll – Simple, powerful, easy-to-use payroll ensuring teams are paid accurately and on time.
- Time – Scheduling, tracking, and paying hourly teams more efficiently.
- Contractors + EoR – A seamless platform for SMBs to manage global teams.
You will join Gusto’s Insights & Operations (I&O) team, empowered by the Chief of Staff to the Head of Product, and collaborate with a community of peers across product areas. I&O partners are trusted operators who bring urgency, clarity, and execution discipline to Gusto’s most important initiatives.
Here’s what you’ll do day-to-day:
- Lead operational mechanisms and activities (roadmaps, OKRs, planning, business reviews).
- Launch and manage cross-functional programs (e.g., End of Year Tax Intake).
- Drive critical initiatives that may be at risk or stalled, bringing urgency and clarity.
- Transform ambiguous, high-potential opportunities into concrete strategies and execution plans.
- Pilot AI-augmented approaches to program management and ops (e.g., AI-assisted payroll prep) and design re-usable automation patterns for AI Agents that can be leveraged by I&O and other Gusto teams.
- Partner on Gusto-wide efforts and other high-impact technical programs.
Here’s what we're looking for:
- 5+ years of experience in business operations, consulting, program management, or product management, ideally in high-growth technology companies.
- Strong program management skills → end-to-end ownership of complex, cross-functional initiatives.
- Operational excellence → proven ability to run team rituals and operating mechanics, including roadmaps, metrics/OKRs, and business reviews.
- Excellent communication and collaboration skills → builds strong cross-functional relationships across engineering, design, product, and business teams.
- Ownership mindset → proactive, comfortable flexing into ambiguous problems at any altitude
- Change leadership → able to guide teams through change with clear communication.
- AI-Native Mindset → Naturally seeks out ways to integrate AI into workflows to accelerate documentation, build smarter systems, and improve decisions
- Alignment with Gusto’s values → customer empathy, grit, and a passion for helping small businesses thrive
Our cash compensation amount for this role is between $158,300 - $195,237/year in Denver and between $185,955 - $229,345/year for New York/San Francisco. 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.
