Health Insurance Renewal Team Leader

Gusto, Inc.

Denver (CO)

Hybrid

USD 92,000 - 113,000

Full time

14 days+

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Job summary

Gusto seeks a Manager for Health Insurance Benefits Advising to lead a licensed advisor team, empowering 10–15 members to deliver best-in-class renewal experiences and expert benefits guidance for small businesses.

You will drive retention and revenue growth, coach for operational excellence, and partner across Product, Carrier Ops, Sales, and CX to optimize tools, training, and processes in a fast-paced, evolving environment.

Qualifications

4-6 years of formal leadership experience in benefits advisory, customer success or renewals, or a similar field.
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 consultative renewal and upsell strategies.
Analytic and strategic thinker with the ability to translate data into insights and actions.
Strong operational skills, proactive approach to process improvement, and previous experience driving initiatives and best practices that improve customer experience.
Ability to evaluate and adopt AI tools strategically to measurably improve advisor productivity, customer retention, and operational efficiency.
Experience with technology/automation solutions such as Salesforce, APIs, and benefits administration platforms.
Executive presence with the ability to align leaders across CX, Sales, and Product, to lead high-impact initiatives.
Customer-first mentality with a first-principles-thinking approach.
Thrives in and can lead a team through a fast-paced environment with constant change and rapid growth.
Able to make measured, objective, data-driven decisions on a daily basis.
Holds (or will be expected to hold) a Life & Health insurance license

Responsibilities

Empower & Coach to Operational Excellence: Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.
Drive retention and revenue growth: Deliver on retention targets by ensuring tailored, high-quality renewal experiences through a customer’s renewal and ongoing benefits experience.
Evolve the customer experience: Use customer feedback and data to identify and drive improved processes and deliver more holistic, outcomes-focused advising. Act as project manager for large-scale, cross-functional initiatives that result in better outcomes for our customers
Lead change management: Guide organization-wide improvements, enabling advisors and managers to adapt and thrive in a dynamic environment.
Foster culture and engagement: Build a culture rooted in Gusto’s values, creating an environment of trust, feedback, and continuous learning.
Work cross-functionally: Partner with Product, Carrier Ops, Sales, and other CX teams to act as the voice of the Advisor by surfacing feedback to improve tooling, training, workflows, and the overall customer experience.
Champion AI integration: Identify high-impact opportunities, coach your team to build critical AI fluency, and shape the future of our customer journey by leveraging new tools for smarter, more proactive customer engagement.