Future Opportunities: Benefits Advocate

Gusto • Chicago, AZ

10d • $21 - $35 • Hybrid

About The Position

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.

Requirements

• 3-6 years of customer experience with 1+ years of full-time experience in health insurance benefits.
• 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.

Nice To Haves

• Account Management experience preferred.
• Life & Health Insurance Producers Licensure preferred.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees