Benefits Advising Leader — Drive Retention & Growth

Gusto, Inc.

Denver (CO)

On-site

USD 92,000 - 113,000

Full time

14 days+

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Job summary

Gusto, Inc. is hiring a Benefits Advising leader to manage a licensed advisor team focused on small business health benefits. You will coach 10–15 advisors, guide renewal cycles, and collaborate with Product, Carrier Ops, Sales, and CX to enhance the customer experience.

A Life & Health license is expected, with a strong track record in renewal strategies and AI-enabled improvements. The role emphasizes customer retention, expansion, and operational excellence in a fast-paced environment, with

Qualifications

4-6 years of formal leadership experience in benefits advisory, customer success or renewals.
Direct experience with small group health insurance (fully insured, level-funded or PEO models) is required.
Proven ability to drive revenue growth, customer retention, and expansion through renewal strategies.

Responsibilities

Empower & Coach to Operational Excellence: provide regular coaching and performance management.
Drive retention and revenue growth through tailored renewal experiences.
Evolve the customer experience by using feedback and data to improve processes.
Lead change management and foster a culture aligned with company values.
Work cross-functionally with Product, Carrier Ops, Sales, and CX teams.
Champion AI integration to improve advisor productivity and outcomes.