Senior Strategic Program Manager

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:

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

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 e