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).
- 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.
- 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.
