Benefits Enrollment Specialist

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: When a small business owner signs up with Gusto, they're trusting us with their team's health coverage. As a Group Fulfillment Specialist, you're the link between our customers and their health insurance carriers — partnering with Onboarding Advocates to ensure every form and detail lands accurately and on time, so coverage is active when employees need it. You'll work across carrier portals, Salesforce, and Gusto's internal systems, and lean into AI tools to work smarter. If you take pride in getting the details right, this role is for you. About the Team: Group Fulfillment is the team that ensures the promise of benefits becomes reality. We sit between health insurance carriers and Gusto's customer-facing teams, shepherding new plans, renewals, and carrier switches across the finish line. We measure ourselves on doing it right and doing it on time — because for the customers we serve, "late" or "wrong" isn't an inconvenience, it's a missed prescription, a delayed procedure, or a stressful call to HR. We take that seriously, and we have a lot of fun doing it together. As an AI-native company, we don't just use technology—it’s the backbone of how we work. We expect all team members to demonstrate digital fluency and a proactive approach to leveraging AI tooling to enhance accuracy, speed, and communication. At Gusto, every team member contributes to a significant daily impact on the lives of those we serve. Here’s what you’ll do day-to-day: End-to-End Enrollment: Manage the intake, submission, and confirmation of group health insurance selections for both new plans and renewals, ensuring all carrier documentation is accurate and complete. Carrier Liaison: Master carrier-specific portals and requirements to efficiently process orders and navigate approval workflows. Eligibility & Compliance: Review customer data against carrier eligibility standards to proactively mitigate errors and ensure high-quality plan adherence. Cross-Functional Collaboration: Partner with Licensed Benefits Advisors and customer-facing teams to deliver benefits packages in full and on schedule. Resolution Management: Act as the primary point of contact for follow-up requests from carriers, resolving information gaps or plan changes with urgency. Process Optimization: Identify and escalate opportunities for workflow enhancements, using your expertise to increase team efficiency and accuracy. Expert Communication: Provide clear, professional guidance on healthcare enrollment to customers and internal partners via written and verbal channels. Here’s what we're looking for: Professional Experience: 6 months to 2 years of professional work experience, ideally within healthcare, health insurance, finance, or a fast-paced startup environment. Technical Fluency: Proficient in Google Workspace, Microsoft Office, Adobe, and Salesforce; as an AI-native company, you will be expected to lean into and master emerging AI tools to drive efficiency. Data-Driven Mindset: Proven success in metrics-based roles where data accuracy and hitting KPIs are central to customer success. Administrative Precision: Strong background in high-volume data entry and processing administrative tasks under tight deadlines and seasonal peaks. Communication & Collaboration: Excellent cross-team communication skills with experience managing professional interactions with external company partners. Adaptability: A skilled problem-solver who is comfortable navigating ambiguity and can pivot quickly in a dynamic operational setting. Self-Directed Execution: Highly self-motivated and capable of working both autonomously and collaboratively to meet individual and team goals. At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto’s compensation philosophy and benefits offerings please view our Total Rewards Approach page. Our cash compensation range for this role is $20.50–$23.08 per hour in Denver. Final offer amounts are determined by multiple factors, including candidate 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.