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Program Manager
Program ManagerGusto • Chicago, IL, US
Program Manager

Program Manager

Gusto • Chicago, IL, US
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Program Manager

At Gusto, we're 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, 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.

This role requires a deep understanding of strategic planning, agile methodology, and program management, with an ability to unify priorities across diverse technical and operational functions. You will collaborate closely with leaders across all CXPI sub-teams, as well as Operations leaders, and CX as a whole, to own the intake, prioritization, sprint execution process, communication, and execution by driving efficiency and ensuring that all initiatives align with strategic CX goals.

As a Program Manager for Workforce Management (WFM) Programs, you will be a key leader within the CX Planning & Insights team, reporting to the Head of Strategy and Tool Administration. You will be responsible for leading and executing strategic programs focused on optimizing our workforce management capabilities, primarily leveraging the NICE WFM platform.

Here's what you'll do day-to-day :

  • Establish and manage the centralized intake process for new work across the Data, Quality, WFM, and Tool Administration sub-teams. Partner with leadership to prioritize the backlog, ensuring resource allocation focuses on the highest-impact initiatives aligned with CX goals.
  • Lead and manage complex, cross-functional programs that span multiple CX teams. Oversee end-to-end delivery, ensuring projects are delivered on time, within scope, and meet business objectives.
  • Act as the execution lead, facilitating agile ceremonies (e.g., sprint planning, daily stand-ups, sprint reviews, retrospectives) for the CXPI sub-teams to ensure a smooth and predictable delivery cadence.
  • Serve as the central communication hub, providing clear, consistent, and transparent updates on program status, risks, and dependencies to stakeholders across all levels, including CX leadership and partner teams.
  • Collaborate with cross-functional teams, including CX Operations, Planning, Scheduling, Intraday Management, Technology, and Analytics, to gather requirements, manage dependencies, and ensure successful program execution that directly benefits the WFM teams.
  • Proactively identify, assess, and mitigate risks and issues that could impact the delivery of projects across the sub-teams. Manage complex dependencies between Data, Quality, WFM, and Tool Administration initiatives.
  • Drive continuous improvement in program management, prioritization, and execution methodologies within the CXPI organization to increase team velocity and efficiency.
  • Develop and maintain comprehensive program documentation, including roadmaps, program plans, status reports, and key decision logs.

Here's what we're looking for :

  • 7-10+ years of progressive experience in program management, agile delivery, or strategic operations, ideally supporting technical or analytical teams within a high-growth environment.
  • Proven experience managing a cross-functional work intake and prioritization process for multiple sub-teams (e.g., Data, Engineering, Operations, or WFM).
  • Deep understanding and practical experience with agile / scrum methodologies and a track record of successfully facilitating sprints and managing program backlogs.
  • Exceptional program management skills, including planning, execution, risk management, and stakeholder communication for complex, multi-faceted initiatives.
  • Strong ability to influence and build consensus across diverse technical and non-technical teams, including high-level cross-functional leadership.
  • Excellent analytical and problem-solving skills with the ability to synthesize complex information from different sources (Data, Quality, WFM) into actionable execution plans.
  • Proficiency in project management and agile tools (e.g., Jira, Asana, NotionAI).
  • Experience in contact center operations or Workforce Management (WFM) environments is a strong plus.
  • Our cash compensation amount for this role is $94,285 / yr to $122,571 / yr in Denver & most major metro locations, and $114,695 / yr to $149,104 / yr 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 Symmetry roles, Gusto's 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 it's 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.

    Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

    Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

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