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 at Gusto. We 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.
About the Role:
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.
About the 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 at scale.
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 10-15 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:
- 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.
Here’s what we're looking for:
- 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 (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, proactive approach to process improvement, and previous experience driving initiatives and best practices that improve customer experience
- 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, to lead high-impact initiatives
- 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
Our cash compensation amount 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 and may vary from the amounts listed above.
At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.
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.
Reliable, consistent presence: We expect regular and predictable attendance, whether you're working in-office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve.
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.
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