Employer Support Specialist

About the role We are looking for an experienced and detail-oriented Customer Support Specialist to join our Employer Servicing team. In this role, you will be the ultimate subject matter expert on our benefits platform and the complex technical systems that power it. You’ll work directly with business leaders and HR admins as their trusted advisor from onboarding through renewal, ensuring they have a seamless experience providing world class benefits to their employees. This is a critical role that blends deep technical knowledge with excellent problem‑solving and communication skills. You’ll thrive in this role if you get energy from solving problems that initially seem impossible and view every customer interaction as an opportunity to improve the product or process. What you’ll do Interface with customers via email, phone, and video conferencing to resolve issues quickly, efficiently, and with a human touch Conduct consultative calls and write detailed explanations that help customers understand complex insurance, compliance, and platform topics Independently investigate and resolve technical problems by reviewing databases, analyzing system logs, and partnering with engineering—then translate findings into clear customer communications Build scalable solutions to customer problems through documentation, macros, videos, and workflow improvements that benefit the entire customer base Partner with product and engineering to advocate for customer needs, provide detailed bug reports, and validate solutions Background we’re looking for 3+ years in customer‑facing operations or technical support within a complex B2B environment (SaaS, fintech, healthtech, or benefits) Excellent written and verbal communication skills—can explain technical concepts clearly to non‑technical audiences Proven ability to handle high volumes with high quality Experience collaborating with engineering teams to resolve customer‑impacting issues Track record of being "the go‑to person" for difficult customer issues and technical questions Experience we’d be particularly excited about Subject matter expertise in benefits administration, payroll systems (Gusto, ADP, Paychex), or HR platforms Experience supporting health insurance, ICHRA, or complex financial/compliance products History of proactively building customer‑facing resources (help articles, videos, templates) that reduce support volume Proficiency with support analytics tools (Zendesk Analytics, Metabase, Looker) to identify trends and measure impact Demonstrable pattern of receiving exceptional customer feedback and serving as a quality benchmark for peers Background in technical account management, implementation, or solutions consulting roles #J-18808-Ljbffr