Senior Manager, 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:

As a Senior Manager, 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 leader and a passionate people manager to drive significant strategic initiatives while fostering the growth and success of a talented team.

You will partner closely with executive leadership across Customer Experience, Product, Engineering, BizTech, Operational Teams, and Sales. As both a player and a coach, you will lead a team of 3-5 Program Managers, empowering them to 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:

People Leadership & Development:

• Lead, coach, and empower a team of 3-5 Program Managers, fostering their craft and capabilities as they drive cross-functional programs.
• Develop a high-performing team that can drive significant impact and influence across the organization.
• Build a psychologically safe team environment, motivate and engage team members, effectively allocate work and projects, and skillfully resolve conflicts while navigating ambiguity.
• Advance team’s use of AI to accelerate work, automate manual processes, and enable the organization to execute on programs at scale.
• Act as a mentor, guiding Program Managers in their development and execution of complex initiatives.
• Willing to roll up your sleeves, lead from the front, and coach the team in our fast-paced, dynamic environment.

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+