Benefits Customer Onboarding Leader

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so 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.

About the Role:

Gusto is seeking a customer-obsessed leader to transform a critical stage of our Benefits customer journey: onboarding. This is a unique opportunity to move beyond traditional operations and solve core business challenges, directly impacting customer retention and success from day one. We are looking for a hands-on change champion who can coach a high-performing team on the front lines while also providing the strategic vision to build a truly value-driven customer experience.

About the Team:

The Onboarding Advocate team is passionate about setting customers up for success with health benefits. We are the first point of contact after the sale and are responsible for ensuring a smooth, confident, and value-driven onboarding experience. By seamlessly managing the complexities of health benefits, we enable our customers to focus on what matters most—their people and their business.

Here’s what you’ll do day-to-day:

• Coach and Develop a High-Performing, Motivated Team:
• Directly empower a team of Onboarding Advocates, providing consistent performance feedback and clear career development.
• Celebrate progress, foster psychological safety, and invest in the personal and professional growth of your team members.
• Champion Value-Driven Onboarding: Lead and inspire your team to move beyond task completion, focusing on delivering successful outcomes that create immediate and lasting value for our customers.
• Drive Improvements to Core Business Metrics: Take a leadership role in analyzing and solving key business challenges, such as new customer churn, by identifying root causes and implementing strategies to improve customer retention from day one.
• Manage to SLAs and Customer Outcomes: Champion our SLA/SLO framework, using data to manage team performance, identify customer friction points, and ensure we are delivering on our promises in a timely and high-quality manner.
• Partner Cross-Functionally: Build a strong, collaborative relationship with our upstream and downstream partners to ensure a seamless customer handoff, improve qualification processes, and create a unified customer experience.

Here’s what we're looking for:

• 3-5+ years of people management experience in customer success, onboarding, renewals, or a similar customer-facing operations role.
• A true passion for coaching and developing individual contributors into high-performing, engaged team members.
• Demonstrated experience analyzing and improving customer retention metrics (e.g., churn, cancel rate, CSAT, time-to-value).
• Strong operational skills with a proactive approach to process improvement and a track record of driving initiatives that improve the customer experience.
• Proven ability to partner effectively with Sales or other Go-To-Market teams to improve the customer lifecycle.
• Skilled collaborator, able to drive progress with peers across the organization.
• An analytical and strategic thinker who can translate data into actionable insights and clear priorities for their team.
• Experience leading a team through ambiguity and change with clear communication and a resilient, positive attitude.
• Eager to leverage AI-powered tools to enhance team efficiency and customer outcomes, with a commitment to developing your team's AI fluency.
• Experience in the health insurance and benefits space is a strong plus. You understand the unique challenges of small business customers and have an interest in scaling processes to support higher-value segments.

Our cash compensation amount for this role is $86,000/yearly - $113,000/yearly in Denver, Phoenix, Chicago and Las Vegas. 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.