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

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