Benefits Advising (Renewals) Leader

About the Role:

Gusto is seeking a leader for our Benefits Advising team who is passionate about providing small business owners and their employees with the best customer experience and expert benefits advice. You will lead a licensed benefits advisor organization by empowering and enabling your individual contributors to deliver a best in class customer experience effectively in a fast paced environment. You’ll be a great fit if you also have experience in effectively managing OKR/team initiatives while also leading a high performing team.

About the Team:

The Benefits Advising team at Gusto is focused on understanding the health insurance needs of small businesses, and consulting on solutions to help their employees thrive. The Benefits Advising leader will empower a team in Gusto’s licensed advising renewal organization, ensuring our customers offer the best health insurance and benefits offerings for their employees. This role will balance both customer impact and operational excellence: you’ll be responsible for driving customer retention, expansion, and exceptional customer experience at scale.

Your team will support small business owners in accessing the best health insurance and holistic benefits offerings - including ancillary coverage, tax-advantaged accounts, and retirement plans like 401(k). Much of this work is centered around small group health insurance, including fully insured and level-funded plans, where tailored guidance is essential for customer success.

You’ll directly empower a team of 10-15 licensed advisors and specialists, guiding them through renewal cycles and enabling them to serve as trusted advisors to our customers.

Here’s what you’ll do day-to-day:

• 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.

Here’s what we're looking for:

• 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—while balancing innovation with risk management, compliance requirements, and maintaining customer trust in a licensed advisory context
• 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

Our cash compensation amount for this role is $86,530/yearly - $106,000/yearly in Phoenix and $92,245/yearly - $113,000/yearly in Denver, 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.