Gusto · 15 hours ago
Future Opportunities: Benefits Advocate
Greater Chicago Area
Full-time
Hybrid
Mid, Senior Level
$21/hr - $35/hr
3+ years expGusto is a company focused on supporting small businesses with payroll, health insurance, and HR services. They are currently seeking motivated customer experience professionals for future health insurance benefits opportunities, where the main responsibilities include providing expert support and building relationships with customers.
Bookkeeping and PayrollEmployee BenefitsEnterprise SoftwareFinancial ServicesFinTechHuman ResourcesSaaSSoftware
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
Qualification
Required
3-6 years of customer experience with 1+ years of full-time experience in health insurance benefits
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
Preferred
Account Management experience preferred
Life & Health Insurance Producers Licensure preferred
Benefits
Health Insurance
401(k)
Company
Gusto
Gusto is an HR and payroll platform that simplifies complex tasks, empowering businesses to focus on what matters most.
1001-5000 employees
H1B Sponsorship
Gusto has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (49)
2024 (54)
2023 (19)
2022 (37)
2021 (24)
Funding
Current Stage
Late StageTotal Funding
$746.1MKey Investors
Friends & Family CapitalT. Rowe PriceAkkadian Ventures
2023-01-28Series Unknown
2022-05-12Series E· $55M
2021-08-10Series E· $175M
Leadership Team
Josh Reeves
Head of Gusto (CEO) and Co-Founder. Building Gusto for the Long Term.
Edward Kim
Co-founder and Head of Technology
Recent News
General Catalyst
2025-12-30
Digital Commerce 360
2025-12-20
2025-12-19
Company data provided by crunchbase