Benefits Advising (Renewals) Manager

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k) s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy . AI is a fundamental part of how work gets done  expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves.

AI experience requirements vary by role and will be assessed during the interview process.

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.

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 r 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.

• 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.

• 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…