Benefits Customer Onboarding Manager

About the Role:

Gusto is seeking a customer-obsessed, tactical leader for our Onboarding Advocate (OA) team. As a People Empowerer (PE), you will be a hands-on coach to a pod of Advocates, ensuring your team provides small business owners and their employees with a world-class health insurance onboarding experience.

Your primary focus is driving team performance by consistently meeting productivity and quality targets, proactively removing tactical hurdles, and coaching your team to excellence. You will play a critical role in scaling Gusto’s benefits business by ensuring our customers have a seamless transition to their new plans.

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. We are actively working to integrate AI tooling to enhance our processes and customer interactions, and we're excited to bring in a leader who can help accelerate this evolution.

Here’s what you’ll do day-to-day:

• Drive Operational Excellence: Manage the daily health of your team's funnel, ensuring all customer milestones and SLAs are met with urgency and accuracy.


• Empower & Coach: Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.


• Remove Roadblocks: Act as the first point of contact for tactical blockers. You will serve as the escalation point in day-to-day execution to ensure your team never feels "stuck."


• Promote Inclusive Growth: Create a psychologically safe and inclusive environment where diverse perspectives are valued and team members feel empowered to do the best work of their lives.


• Iterate on Process: Constantly analyze team performance data to identify and solve for moments of customer pain or internal friction, refining processes to make them simpler, more efficient, and in direct service to the customer experience.


• Partner Cross-Functionally: Collaborate closely with upstream Advisory and downstream Fulfillment partners to ensure clean handoffs and a unified customer experience.

Here’s what we're looking for:

• 1-2+ 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.


• Exceptional verbal and written communication skills with the ability to deliver feedback that is both direct and supportive.


• Strong operational skills with a proactive approach to process improvement and a track record of driving process optimization efforts that improve the customer experience.


• 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 $74,285/yearly - $91,000/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.