Senior Manager, Program Manager

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stufflike payroll health insurance 401(k)s and HRso owners can focus on their craft and customers. With teams in Denver San Francisco and New York were proud to support more than 400000 small businesses across the country and were 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 Gustos 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 Gustos 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.

Heres what youll 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 teams 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.

Heres what were 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.
• 4 years of demonstrated success leading coaching and managing individual contributors including experience leading leaders.
• 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.
• Demonstrated leadership skills including the ability to build a psychologically safe team motivate and engage teams allocate work resolve conflicts and handle ambiguity.
• Proficiency in program management software like Asana Notion Airtable and JIRA.
• Experience with Excel/Google Sheets and Gsuite is strongly encouraged.

Our cash compensation range for this role is $154045 to $207305 in Denver & Los Angeles and $181275 to $223573 in Seattle New York & San Francisco. Final offer amounts are determined by multiple factors including candidate location experience and expertise and may vary from the level and 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 Symmetry roles Gustos 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.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

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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