Product Support Specialist

About the role

In this role, you will be the ultimate subject matter expert on our benefits platform and the complex technical systems that power it. This role is not your typical support role – it will require you to build strong technical expertise, leverage strong problem‑solving skills, and use project management skills to strategically improve our support systems, processes, and product quality.

You will work directly with business leaders and HR admins as their trusted advisor, ensuring they have a seamless experience providing world‑class benefits to their employees. You will coordinate with cross‑functional teams, including Engineering, Product, and Sales, to drive them to resolution. A deep understanding of our platform will allow you to engage with these teams effectively, analyze data to inform decisions, and propose solutions that drive operational efficiency.

If you are looking for a launchpad to your career at a high‑growth technology company, this role is for you.

• Analyze, troubleshoot, and resolve complex issues through direct customer interface (email, phone, video conference)
• Conduct consultative calls and write detailed explanations that help customers understand complex insurance, compliance, and platform topics
• Develop product and platform expertise, working closely with Engineering, Product, and Operations teams to diagnose and resolve user issues
• Independently investigate and resolve technical problems by reviewing databases, analyzing system logs, and partnering with engineering—then translate findings into clear customer communications
• Build partnerships and relationships with large mid‑market and enterprise accounts
• Create and refine documentation to empower users to resolve issues via self‑service, reducing dependency on support teams
• Collaborate and advocate with Product and Engineering to proactively improve the platform based on user feedback, ensuring long‑term product reliability
• Lead cross‑functional projects aimed at identifying inefficiencies in current processes and drive the implementation of long‑term solutions

• 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
• Experience managing and developing large client relationships
• Track record of being "the go‑to person" for difficult customer issues and technical questions

• Proficiency in SQL for data analysis and querying, with the ability to interpret datasets
• Experience working with HR administrators on billing reconciliation and payroll deduction reporting
• Experience at fast‑growing technology companies
• History of proactively building customer‑facing resources (help articles, videos, templates) that reduce support volume