Senior Strategic Program Manager

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

Core Experiences is at the heart of Gusto's product platform — building customer-facing products and foundational capabilities used across R&D. We're looking for an exceptional Senior Strategic Program Manager to help scale this impactful group by owning operational cadences and leading cross-functional program execution.

This role is perfect for someone who thrives in complexity, sees around corners, and builds the systems that make high-impact work possible. You'll play a central role in delivering on ambitious priorities like AI and Gusto's customer communications strategy. This role is a unique opportunity to help drive and support high priority initiatives for Gusto's Core Experiences group. You will be empowered by the Chief of Staff to the Head of Core Experiences, joining a world-class Insights and Operations team balancing strategy, operations, and special projects to create a world where work empowers a better life.

About the Team

The Core Experiences Platform teams encompass the foundational data models, APIs, and UX concepts (or "commons") that teams across Gusto leverage to build high quality, cohesive experiences at scale. We think globally about how to craft a thoughtful system of apps and experiences — considering the full stack — so that App teams can focus more locally on solving their unique jobs to be done. This work is critical to ensuring that Gusto functions and feels like one integrated, connected experience, where concepts, data, and UX patterns have shared meaning and where customers can build their own understanding and confidence because the experience is predictable, consistent, easy to use and feels custom-built for the unique needs of their business.

Here's what you'll do day-to-day

Strengthen operational rhythms — Drive the Core Experiences leadership team's operating cadence. Plan and facilitate org-wide rituals (weekly meetings, onsites, planning cycles) with clear templates, timelines, and coordination so the team runs smoothly.

Keep strategic programs on track — Lead operations for high-priority initiatives (including customer-facing AI initiatives), ensuring alignment on timelines, goals, and success criteria across complex stakeholder groups.

Connect the dots across teams — Partner with App teams, other platform teams, and teams across Gusto to align priorities, surface tradeoffs, and allocate resources effectively. Identify and mitigate risks early, leading operational readiness so programs succeed post-launch.

Build scalable systems — Design and evolve processes that make Core Experiences more effective. Maintain centralized documentation hubs and create repeatable enablement tools (e.g., platform roadshows, adoption toolkits) to support cross-team knowledge sharing.

Here's what we're looking for

7–10 years of experience in analytical, operating roles at high-growth startups

5–7 years in program or project management, ideally in a high-growth tech company

Experience within a cross-functional product organization (preferred)

Proven ability to create operational excellence through strategic cadence and discipline

Strong organizational skills; ability to manage multiple priorities in a fast-paced environment

Proficiency in project management methodologies and tools

Experience in strategic planning and translating strategy into actionable plans with KPIs / OKRs

Excellent communication and interpersonal skills

Strong problem-solving and analytical abilities

Deep empathy for small business customers

Ability to flex between strategic and tactical work

Skill at keeping priorities on track and communication flowing

A passion for helping others

Bonus if you've led programs in AI or other innovative technology areas, with an eye toward cross-functional alignment and execution

Compensation

Our cash compensation amount for this role is 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.

Location & Office Expectations

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.

Equal Opportunity Employer

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.

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