Head of Strategy and Tool Administration

Gusto

Gusto

San Francisco, CA, USA · New York, NY, USA · Denver, CO, USA
USD 163,200-204k / year
Posted on Jul 4, 2025


About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.

About the Role:

We are seeking a dynamic and experienced Head of Program Management and Tool Administration to lead the strategic and operational aspects of our CX Planning & Insights programs. This pivotal role will be responsible for fostering agile and scrum practices within the team, ensuring efficient and effective delivery of key initiatives. Additionally, you will own the administration and optimization of critical tools, including NICE Workforce Management (WFM), performance management platforms, and routing configurations, ensuring they are aligned with our business needs and empower our CX teams.

About the Team:

This is a unique opportunity to blend your expertise in agile methodologies and program management with your technical acumen in administering and optimizing essential CX technology. You will be a key leader in driving operational excellence and enabling our CX Planning & Insights team to deliver impactful results.

Here’s what you’ll do day-to-day:

Planning and Strategy Leadership:

  • Lead and mentor a team of planning and strategy leads, routing analysts, and tool administrators, fostering a collaborative and high-performing environment.
  • Establish and champion consistent program management methodologies, standards, and best practices across the CX Planning & Insights group, with a strong emphasis on agile and scrum frameworks.
  • Oversee the planning, execution, and delivery of complex, cross-functional programs and projects, ensuring they are on time, within budget, and meet strategic objectives.
  • Facilitate agile ceremonies (e.g., sprint planning, daily stand-ups, sprint reviews, retrospectives) and coach teams on agile principles and practices.
  • Identify and mitigate program risks and issues, proactively developing and implementing solutions.
  • Develop and maintain program documentation, including project plans, timelines, communication plans, and status reports.
  • Communicate program progress, risks, and dependencies effectively to stakeholders at all levels.
  • Drive continuous improvement in program management processes and agile practices within the organization.

NICE WFM Administration & Optimization:

  • Lead the team responsible for the primary administration for the NICE WFM platform, responsible for its configuration, maintenance, and optimization.
  • Collaborate with stakeholders to understand workforce planning needs and translate them into effective NICE WFM configurations.
  • Help WFM Administrator troubleshoot NICE WFM issues, working with internal IT and external vendors as needed.
  • Stay up-to-date on NICE WFM features and best practices, proactively identifying opportunities for improvement and efficiency gains.

Performance Management & Routing Configuration:

  • Lead the administration and optimization of performance management tools used within the CX organization.
  • Collaborate with CX leadership to understand performance management requirements and configure tools to support these needs.
  • Manage and optimize routing configurations across various CX channels (e.g., phone, email, chat) to ensure efficient and effective customer interactions.
  • Work closely with contact center technology teams to implement and maintain routing strategies.
  • Analyze routing performance data to identify areas for improvement and implement necessary adjustments.
  • Ensure performance management and routing configurations are aligned with business objectives and service level agreements (SLAs).

Here’s what we're looking for:

  • 10+ years of leadership experience, including leading leaders, with 12+ years in program management, strategy, or planning—strong focus on agile/scrum
  • Deep expertise in Workforce Management (WFM) strategy and execution across complex contact centers; NICE IEX experience preferred
  • Proven success mentoring program management teams and applying agile frameworks (Scrum, Kanban, Lean); CSM (Certified Scum Master) or equivalent certification
  • Strong skills in workforce optimization: capacity planning, headcount modeling, and vendor collaboration for scalability
  • Experienced in WFM platform administration and development, with strong technical aptitude and adaptability to new tools
  • Analytical mindset with expertise in data reporting, performance trend analysis, and translating insights into action

Our cash compensation amount for this role is $163,200/yearly to $204,000/yearly in Denver & most major metro locations, and $191,200/yearly to $239,000/yearly 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.


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.

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