Future Opportunities: Benefits Advocate

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. 

Submit your interest to join our CX team!

Gusto is seeking customer experience professionals who thrive in a fast-paced, consultative environment and are interested in being considered for future start dates in 2026. If you’d like to be considered for future opportunities with our team, please complete the form below and upload your resume. 

While start dates are still being determined for 2026, we’d love to connect! Does this sound like you? Apply below!

About the Role:

Gusto is seeking motivated, customer-centric professionals interested in being considered for future health insurance benefits customer experience opportunities in 2026. These roles are ideal for customer-facing benefits professionals who thrive in a fast-paced, consultative environment and are passionate about helping small businesses succeed.

As a seasoned Health Insurance Benefits Advocate, you will act as the single point of contact for all benefits support and renewal inquiries, enhancing user experience and serving as a subject matter expert for Gusto’s core products. You’ll help employers get group benefits for the very first time, and then help those employers continue to make important benefits decisions on an annual basis. Together, we’re not just simplifying benefits — we’re helping small businesses offer competitive, people-first benefits that support happier, healthier teams.

Here’s what you’ll do day-to-day:

• Own the customer journey by building trust, rapport, and partnership with customers through inbound and outbound phone, email, and Zoom interactions.
• Provide passionate, opinionated, consistent, expert, reliable support as a point of contact for health insurance benefits inquiries. 
• Partner with internal teams to address and resolve customer inquiries and concerns throughout the benefits renewal process.
• Leverage AI‑assisted tools to accelerate research and communication while upholding accuracy, compliance, and Gusto’s voice.
• Identify churn risk and quickly act to deliver solutions to mitigate the risk of churn, using your health insurance benefits and product knowledge and unique understanding of each individual customer.
• Build and maintain relationships built on trust and collaboration with admins to better understand and anticipate their needs.
• Think creatively, pivot quickly, live in ambiguity, and collaborate strategically. You will be required to expand your critical thinking skills and creatively problem-solve across all areas of the business, with an understanding of a variety of stakeholders and needs. 

Here’s what we're looking for:

• 3-6 years of customer experience with 1 years of full-time experience in health insurance benefits. 
• Account Management experience preferred. 
• Life & Health Insurance Producers Licensure preferred. 
• Proven ability to proactively and reactively support customers, driving their success, happiness, and loyalty through expert guidance and creative problem-solving.
• Ability to synthesize and communicate complex subjects clearly and effectively, both verbally and in writing, with customers and internal partners.
• Experience with Salesforce, Zoom, Google Suite, Google Calendar, Gmail, and Chili Piper.
• Excels in balancing inbound calls, scheduled meetings, and email inquiries while managing and prioritizing multiple high-priority resolutions effectively.

This posting represents a general talent pipeline that spans multiple levels within our CX team. Final compensation will be determined based on the specific role, level, and experience alignment. The estimated compensation range for these roles is $21.00–$35.00 per hour.

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.