About Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re 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 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. 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.
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, 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 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 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 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, 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 $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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Gusto Denver, Colorado, USA Office
Gusto's Denver office is located right off of the 16th Street Mall, a pedestrian-friendly area packed with shopping, restaurants, and attractions. Many Gusties take RTD transit, while others bike and drive in to the office.
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