Benefits Advisory Leader: Scale Renewals with AI

Monograph; Denver (CO); Hybrid; USD 87,000 - 113,000; Full time

Benefits offered by this job

Equity (RSUs)

Competitive base pay

Hybrid work model

Job summary

Gusto seeks a growth-oriented leader to head the Benefits Advising team, empowering 10–15 licensed advisors. You will drive renewal excellence, advise on health benefits, and balance customer outcomes with operational efficiency in a fast-paced environment.

You will partner with product, carrier ops, and sales to optimize renewals, retention, and expansion, leveraging AI tools while ensuring compliance and trusted guidance in a licensed advisory context.

Qualifications

• 4-6 years of formal leadership in benefits advisory or renewals.
• Direct experience with small group health insurance is required.
• Proven ability to drive revenue growth and retention through renewal/up-sell strategies.
• Analytic and strategic thinker; translate data into actions.
• Experience leading AI-enabled initiatives to improve advisor productivity.

Responsibilities

• Empower and coach to operational excellence with regular 1:1s and reviews.
• Drive retention and revenue growth through tailored renewal experiences.
• Evolve the customer experience using feedback and data; lead cross-functional initiatives.
• Lead change management across the organization.
• Foster a culture aligned with company values focusing on trust and learning.
• Collaborate with Product, Carrier Ops, Sales, and CX teams to improve tooling and workflows.
• Champion AI integration to enhance advisor efficiency and customer engagement.

Skills

Leadership

Benefits advisory

Health insurance

Revenue growth

Data analytics

Operations management

AI tool adoption

Salesforce

APIs

Benefits platforms

Education

Life & Health license

Tools

Salesforce

APIs

Benefits administration platforms

Job description

Gusto seeks a growth-oriented leader to head the Benefits Advising team, empowering 10–15 licensed advisors. You will drive renewal excellence, advise on health benefits, and balance customer outcomes with operational efficiency in a fast-paced environment.

You will partner with product, carrier ops, and sales to optimize renewals, retention, and expansion, leveraging AI tools while ensuring compliance and trusted guidance in a licensed advisory context.