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Salary: USD 150,640 - 218,325 / annual
Gusto is seeking a Strategic Program Manager to lead high-priority, cross-functional programs that shape the future of customer experience in an AI-enabled environment. You will partner closely with executive leadership across Customer Experience, Product, Engineering, Data, Design, and Operations to navigate complex challenges, execute large-scale initiatives, and bring Gusto's strategic vision to life.
The Program Management Office (PMO) is at the heart of planning and executing Gusto's highest priorities. As a Strategic Program Manager, you will drive impact through crystal-clear priorities, robust roadmaps, and organizational rigor, committed to building operational excellence and continuously improving service delivery.
Day-to-day responsibilities include:
**Strategic Program Management & Execution:**
- Lead and drive high-priority, cross-functional programs, taking full ownership for success or failure
- Develop and manage comprehensive program and project plans, charters, and roadmaps for initiatives interfacing with Product, Engineering, and Customer Experience
- Identify frameworks and design principles for programs that generate success, proposing creative and effective solutions
- Collaborate with Engineering, Product, Design, and Business Technology teams to solve impactful problems across multiple initiatives, with understanding of AI-driven solutions
- Distill complex technical concepts into clear, actionable updates for stakeholders at all levels
**Operational Readiness & Influence:**
- Exhibit systems-thinking approach to programs and decisions, demonstrating deep understanding of 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, providing data-driven insights and recommendations to enhance CX strategy
- Consistently demonstrate influence with executive-level stakeholders through collaboration and presentations, serving as trusted thought partner
- Contribute to continuous improvement of team operating models, tooling (Asana, JIRA, Confluence), and reporting mechanisms
Gusto supports more than 500,000 small businesses nationwide, handling payroll, health insurance, 401(k)s, and HR services. All full-time employees receive competitive base pay, benefits, and equity (RSUs). AI is a fundamental part of how work gets done at Gusto, and all team members are expected to actively engage with AI tools relevant to their role.
Office expectations: Employees based in Denver, San Francisco, New York, or Scottsdale will be expected to work from the office approximately 2-3 days per week (or more depending on role). When approved to work from other locations, a secure, reliable, and consistent internet connection is required.
**Requirements:**
- 8+ years of experience in program management, operations, and/or project management roles, with 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 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 small business customers
- Strong desire for continuous process improvement and 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 strongly encouraged
