Senior Leader, Benefits Advising

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stufflike payroll health insurance 401(k)s and HRso owners can focus on their craft and customers. With teams in Denver San Francisco and New York were proud to support more than 400000 small businesses across the country and were building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

About the Role:

The Senior Leader Benefits Advising will empower Gustos 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: youll be responsible for building mechanisms that drive customer retention expansion and exceptional customer experience at scale. This role will be at the forefront of helping integrate AI and automation into the advising experience ensuring our teams leverage technology responsibly while maintaining the human touch that builds trust with small business owners.

About the Team:

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.

Youll directly empower a team of 46 frontline leaders and a total organization of 3050 licensed advisors and specialists guiding them through renewal cycles and enabling them to serve as trusted advisors to our customers.

Heres what youll do day-to-day:

• Directly oversee and develop leaders: Coach and empower 46 leaders and their teams of licensed advisors.
• Lead CX strategic direction: Define and execute the renewal and advising strategy for Gustos benefits customers.
• Drive retention and revenue growth:
  • Deliver on retention targets by ensuring tailored high-quality renewal experiences.
  • Build playbooks to expand coverage across ancillary tax-advantaged and retirement offerings.
  • Partner with Finance and CX leadership to establish and achieve revenue goals tied to renewals.
• Redesign advisor workflows to integrate AI and automation tools (e.g. Salesforce Next Best Action AI-powered recommendations) enabling advisors to spend more time on high-value customer engagement while ensuring responsible AI practices and human-in-the-loop oversight for critical decisions
• Champion compliance ethics and trust ensuring all advisor recommendations meet regulatory standards while maintaining customer-first outcomes.
• Foster culture and engagement: Build a culture rooted in Gustos values creating an environment of trust feedback and continuous learning.
• Lead change management: Guide organization-wide improvements enabling advisors and managers to adapt and thrive in a dynamic environment.
• Evolve the customer experience: Use customer feedback and data to refine renewal processes and deliver more holistic outcomes-focused advising.

Heres what were looking for:

• 5 years of leadership experience in customer success account management or benefits/insurance advisory including leading leaders.
• Proven ability to drive revenue growth customer retention and expansion through consultative renewal and upsell strategies.
• Direct experience with small group health insurance (fully insured and level-funded models) is required.
• Background in building scalable processes and mechanisms to support customer outcomes.
• Ability to evaluate and adopt AI tools strategically to measurably improve advisor productivity customer retention and operational efficiencywhile 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 and communicate a compelling vision to both frontline teams and senior stakeholders.
• Customer-first mentality with a first-principles-thinking approach.
• Thrives in a fast-paced environment with constant change and rapid growth.
• Able to make measured objective data-driven decisions on a daily basis.

Our cash compensation amount for this role is$119000/yearly to $154000/yearly in Denver Las Vegas Chicago Phoenix. Final offer amounts are determined by multiple factors including candidate location experience and expertise and may vary from the amounts listed above.

Gusto has physical office spaces in Denver San Francisco and New York City. Employees who are 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 Gustos subsidiary whose physical office is in Scottsdale.

Note: 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. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject toGustos Applicant Privacy Notice.