Head of CX Planning and Insights

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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 300,000 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

Job Summary

This is a leadership role reporting to our Head of CX (Chief Customer Officer) within CX. Gusto’s CX organization is the linchpin of our world-class experience. With their passion, insight, and customer advocacy, the CX team has helped Gusto maintain industry-leading NPS scores while serving over 300,000 customers. We strive to positively influence millions of businesses and hundreds of millions of employees across the county.

We seek a dynamic and experienced individual to join our team as the Head of Planning and Insights (CXPI). In this role, you will lead the strategy, execution, and continuous improvement of our CX Planning and Insights function.  You will be responsible for deploying operational and insightful dashboards to support CX Leadership in decision making and supporting their key business objectives. You are also responsible for annual, monthly, weekly, and daily resource planning to ensure operations can meet the business needs while driving productivity improvement strategies. You’ll work closely with leaders across the CX organization to proactively identify and scope their business intelligence and data analysis needs, provide recommendations on the best metrics to measure and watch and turn data into critical insights that can be used to make sound business decisions. Additionally, you'll drive insights that fuel business growth and enhance both product and customer experiences.

Here’s what you’ll do day-to-day:

  • Lead the team, responsible for frontline resource planning and providing data-driven insights across the CX org, including customer care, benefits operations, payroll operations and revenue operations inclusive of our sales and onboarding teams. 
  • Work closely with product, marketing, and segment leaders to provide key insights, analytics and trend analysis to enable effective marketing and retention strategies, and drive broader platform improvements.
  • Develop and execute a comprehensive CX Data and Insights Strategy that aligns with overall business goals.
  • Lead the development of a robust Customer Service Quality Assurance Strategy, establishing consistent quality standards across CX and implementing industry-leading programs and methodologies supported by technology.  
  • Lead the Workforce Management (WFM) team, who are responsible for the development of strategic workforce management systems and solutions across CX, Operations, and Revenue in multiple complex operating environments across the enterprise to support internal and external customers and vendors
  • Stay current with industry trends, best practices, and emerging technologies in data and insights. Incorporate innovative approaches and tools to enhance the impact and efficiency of data and insights, including the use of AI and LLM.
  • Provide independent analysis of operational performance, offering data-driven recommendations based on industry best practices.

Here’s What We’re Looking for:

  • 12+ years minimum of people management experience in CX and technology-focused organizations.
  • 8+ years leading other managers, setting strategic visions, and empowering high-performance teams
  • Proven CX leader who has scaled support teams in highly regulated industries.
  • Prioritization of a customer-first mindset, using first-principle thinking to innovate and create a world-class onboarding experience resulting in exceptional outcomes for Gusto, our customers, and our employees. 
  • Proven success in driving organizational change in large, matrixed organizations, with equal emphasis on process and outcome. 
  • Strong analytical skills: Comfortable with interpreting multiple customer data points to form hypotheses and make data-driven decisions.
  • Strong collaboration and stakeholder management skills, with the ability to influence at all levels.
  • Willingness to actively engage in hands-on work, especially in the initial stages of building this function.
  • Exceptional storytelling, communication, and presentation skills with audiences at all levels, including Senior Executives and Board Directors.
  • Ability to provide support and advise Senior Leaders on CX strategies and objectives.
  • Proven track record of delivering high customer satisfaction while also driving operational efficiencies.
  • Ability to think globally and strategically, influencing change across multiple business units and functions.
  • Thrives in a fast-paced environment with constant change, rapidly growing teams, with a passion for data-driven decision making on a daily basis.
  • Proficiency in analytic tools, like Redash, Tableau, and other BI platforms preferred.
  • Experience with Workforce Planning and optimization tools. 

Location and Travel

Gusto has physical office spaces in Denver, San Francisco, and New York City. All Gusto roles posted in these metro areas come with the expectation of working from the office on designated days approximately 2-3 days per week (or more depending on role and business travel expectations). 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 role would include travel (~1x/month).


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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