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. 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 perks 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 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.

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. 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 : 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. 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 (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 ~ Able to make measured, objective, data-driven decisions on a daily basis ~ Holds (or will be expected to hold) a Life & Health insurance license 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 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. 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.

Personal information collected and processed as part of your Gusto application will be subject to Gusto’s Applicant Privacy Notice. #

📌 Benefits Advising (Renewals) Manager (Quinte West)
🏢 Gusto
📍 Quinte West