Strategic Program Manager

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 500,000 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: As a Strategic Program Manager at Gusto, you will play a pivotal role in shaping the future of our customer experience within an increasingly AI-enabled environment. This is a unique opportunity for a seasoned program manager to drive significant strategic initiatives at Gusto. You will partner closely with executive leadership across Customer Experience, Product, Engineering, Data, Design, and Operational Teams. You will navigate complex challenges, execute large-scale cross-functional programs, and bring Gusto's strategic vision to life. You will set the standard for how Gusto prepares the business for critical technical and operational change, ensuring our service model evolves seamlessly with new product and feature launches. Your work will demand a deep customer obsession, strategic foresight, meticulous attention to detail, and a highly creative approach to problem-solving. About the Team: The Program Management Office (PMO) is at the heart of planning and executing Gusto's highest priorities impacting the customer. Directly supporting multiple teams, we drive impact through crystal clear priorities, robust roadmaps, and organizational rigor. We are committed to building operational excellence and continuously improving how we deliver outstanding service experiences. Here’s what you’ll do day-to-day: Strategic Program Management & Execution: Lead and drive high-priority, cross-functional programs for Gusto, taking full ownership for their success or failure. Develop and manage comprehensive program and project plans, charters, and roadmaps for initiatives that interface with Product, Engineering, and Customer Experience. Expertly identify frameworks and design principles for programs that will generate success, and propose new, creative, and effective solutions. Collaborate with Engineering, Product & Design, and Business Technology teams to solve impactful problems across multiple initiatives, with an understanding of AI-driven solutions. ​​Distill complex technical concepts into clear, actionable updates for stakeholders at all levels. Operational Readiness & Influence: Exhibit a systems-thinking approach to any program or decision, demonstrating a deep understanding of the interdependent relationships between teams, organizations, product/service offerings, and operational needs. Create and implement robust AI-enabled readiness plans to prepare the business for weekly and monthly launches, ensuring smooth change management. Shape effective reporting mechanisms and cadences for large audiences, both vertically and horizontally, providing data-driven insights and recommendations to enhance CX strategy. Consistently demonstrate influence with executive-level stakeholders through collaboration and presentations, serving as a trusted thought partner for leaders across the organization. Contribute to continuous improvement of team operating models, tooling (e.g., Asana, JIRA, Confluence), and reporting mechanisms Here’s what we're looking for: 8+ years of experience in program management, operations, and/or project management roles, with a proven track record of executing large-scale, complex projects spanning multiple stakeholders and organizations. Aptitude for understanding technical workstreams, engineering requirements, and how products/features map to operational needs for launch and change management; experience with AI-driven programs is required. Strong understanding of service design principles and methodologies. Stakeholder and project management mastery, with a proven ability to drive clarity, recommendations, and alignment amidst competing interests and complexities. Insightful quantitative analysis skills, paired with strong critical thinking and sound business judgment. Deep empathy and obsession for our small business customers. Strong desire for continuous process improvement and a passion for driving efficiency, with demonstrated examples of leveraging AI. Executive presence and exceptional ability to influence cross-functional, senior leaders and drive change. Comfortable analyzing, questioning, and leveraging data to inform decisions. Strong verbal and written communication skills, as well as data visualization and presentation skills. Proficiency in program management software like Asana, Notion, Airtable, and JIRA. Experience with Excel/Google Sheets and Gsuite is strongly encouraged Our cash compensation amount for this role is $150,640 to $185,789 in Denver & most major metro locations and $177,020 to $218,325 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 S