Lead / Manager

Gusto is seeking a leader for its Benefits Advising team, 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, empowering individual contributors to deliver a best-in-class customer experience in a fast-paced environment. You'll be a great fit if you have experience managing OKR/team initiatives while leading a high-performing team.

The Benefits Advising team focuses on understanding the health insurance needs of small businesses and consulting on solutions to help their employees thrive. The leader will empower a team in Gusto's licensed advising renewal organization, ensuring customers offer the best health insurance and benefits offerings. This role balances customer impact and operational excellence, driving customer retention, expansion, and exceptional customer experience at scale. The team supports small business owners in accessing health insurance and holistic benefits, including ancillary coverage, tax-advantaged accounts, and retirement plans like 401(k). Much of the work centers on small group health insurance, including fully insured and level-funded plans. You'll directly empower a team of 10-15 licensed advisors and specialists through renewal cycles.

• Empower & Coach to Operational Excellence: Provide regular coaching and performance management via 1:1s and monthly reviews, focusing on technical mastery, customer-centricity, and hitting KPIs.
• Drive retention and revenue growth: Deliver on retention targets by ensuring tailored, high-quality renewal experiences.
• Evolve the customer experience: Use customer feedback and data to drive improved processes and deliver more holistic, outcomes-focused advising.
• Act as project manager for large-scale, cross-functional initiatives.
• Lead change management: Guide organization-wide improvements, enabling advisors and managers to adapt and thrive.
• Foster culture and engagement: Build a culture rooted in Gusto's values.
• Work cross-functionally: Partner with Product, Carrier Ops, Sales, and other CX teams to act as the voice of the Advisor.
• Champion AI integration: Identify high-impact opportunities, coach your team to build critical AI fluency, and shape the future of the customer journey.

• 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 consultative renewal and upsell strategies.
• Analytic and strategic thinker with the ability to translate data into insights and actions.
• Strong operational skills and proactive approach to process improvement.
• Ability to evaluate and adopt AI tools strategically to improve advisor productivity, customer retention, and operational efficiency, while balancing innovation with risk management and compliance.
• 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.
• 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.

Cash compensation 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.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, whose physical office is in Scottsdale. The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.

All full-time employees receive competitive base pay, benefits, and equity (RSUs).