Senior Lead, Program Manager

Gusto • Denver, CO;New York, NY;San Francisco, CA;Seattle, WA;Los Angeles, CA • 2d ago

About the Role:

As a Senior Lead, 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, BizTech, Operational Teams, and Sales. 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 range for this role $150,640 to $202,057 in Denver & Los Angeles and $177,020 to $218,325 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.

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