When Member Support & Client Operations Specialist Remote · Full time

The Member Support & Client Operations Specialist will be responsible for service delivery excellence to our customers and members. They will provide outstanding support to members undergoing changes impacting their healthcare and employment, and drive When's value impact for our customers.


The Opportunity:

When is a Chicago-based, venture-backed company that has built a novel AI-driven health insurance marketplace and post-employment platform. Our product will transform how companies offboard employees and how people manage their transition between jobs. 


We are currently hiring for a Member Support & Client Operations Specialist. This is an extremely important role for our team. We need someone who has experience working in a B2B SaaS client success role and an individual member support role. This role will support our customers (employers) and their current and former employees.  


This role will be responsible for driving engagement among our customers’ former employees to ensure When delivers value for our customers; maintaining healthy relationships with customers to achieve revenue retention goals; and helping to establish our customer success and member support functions. 



  • Proactively engage with our customers’ former employees to and manage inbound support inquiries. Provide high-touch, white-glove offboarding support and knowledgeable health insurance expertise.
  • Improve member engagement rates, employee platform utilization, and enrollment through When.
  • Identify opportunities for improvement and collaborate with product, technology, and marketing teams to drive member engagement and conversion.
  • Work with leadership to develop the customer success and member support functions. 
  • Monitor customer relationship health and maintain engagement by establishing best practices such as usage of CRM platforms, hosting QBRs, etc.
  • Assist with new customer implementations and manage ongoing customer requests in partnership with cross-functional teams. 
  • Ability to learn our back office technology and work closely with product and technology teams to recommend system improvements. 
  • Establish customer success and member support analytics to measure baseline performance, identify opportunities for improvement, and measure impact of projects & initiatives.


  • Bachelor’s Degree.
  • Minimum 2 years experience working in an operations, customer success, or member support capacity for an insurance business, ideally a brokerage or MGA/MGU.
  • Absolute passion for helping people and building relationships with customers.
  • Team player with the ability to work in a startup environment, juggling multiple tasks simultaneously and navigating ambiguity.
  • Strong written and verbal communication skills in both a customer-facing and member-facing capacity.
  • Comfortable working remote and using web-based meetings with our team, our partners and clients.
  • Excellent organizational, task and time-management skills.
  • You’ll be interacting with our customers and their former employees who may be undergoing job loss – you must be professional, respectful, and nice.



We offer a competitive salary plus commission, we pay 100% of your health insurance, and more!


This position reports to:

Head of Product


Location & Travel:  

Remote with minimal travel to attend conferences and occasional client meetings.


$45,000 - $55,000 per year