Why This Job is Featured on The SaaS Jobs
This onboarding leadership role sits at a pivotal point in the SaaS revenue engine: the handoff from closed-won to first value. In benefits administration software, onboarding is not a lightweight implementation step but a high-stakes moment where product complexity, compliance realities, and customer confidence converge. The remit signals a company treating onboarding as a lever for retention, not just a support function.
For a SaaS career, the role builds durable operating muscle across the post-sale lifecycle. It combines frontline people leadership with metric-driven problem solving around churn, time-to-value, and service reliability, all core to subscription economics. The emphasis on cross-functional partnering with upstream and downstream teams also reflects how modern SaaS organizations scale customer outcomes through shared processes, not isolated departments.
This position will suit a manager who enjoys coaching customer-facing teams while also owning the mechanics behind performance, quality, and continuous improvement. It is a strong fit for someone who prefers using data to diagnose friction, can translate strategy into daily execution, and is motivated by improving customer outcomes in a regulated, detail-oriented SaaS domain.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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.
