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Senior Leader, Benefits Advising

Denver, CO;Las Vegas, NV;Chicago, IL;Phoenix, AZ

 

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy. 

About the Role:

The Senior Leader, Benefits Advising will empower 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 building mechanisms that drive customer retention, expansion, and exceptional customer experience at scale.

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.

You’ll directly empower a team of 4–6 frontline leaders and a total organization of 30–50 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:

  • Directly oversee and develop leaders: Coach and empower 4–6 leaders and their teams of licensed advisors.
  • Lead CX strategic direction: Define and execute the renewal and advising strategy for Gusto’s 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), enabling advisors to spend more time on high-value customer engagement.
  • 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 Gusto’s 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.

Here’s what we're looking for:

  • 5+ years of leadership in customer success, account management, or benefits/insurance advisory, including leading leaders
  • Proven track record in revenue growth, retention, and expansion through consultative renewals and upsells
  • Required experience with small group health insurance (fully insured and level-funded models)
  • Skilled at building scalable processes and leveraging technology/automation (Salesforce, APIs, benefits admin platforms)
  • Executive presence: able to align CX, Sales, and Product leaders and inspire both frontline teams and executives
  • Customer-first mindset with strong data-driven decision-making and adaptability in fast-paced, high-growth environments
  • Holds (or will be expected to obtain) Life & Health insurance license

Our cash compensation amount for this role is $119,000/yearly to $154,000/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, Gusto's 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 it's 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 to Gusto's Applicant Privacy Notice.

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