[Hiring] Director, Member Support Operations @When

Role Description

We are hiring a Director, Member Services Operations: an operational expert who executes and scales member services through tools, data, and automation while delivering a superior member experience. You will lead the Member Services team: the licensed agents who guide members through coverage transitions, ICHRA enrollment, and Medicare decisions, along with specialists in enrollment, licensing, and other key roles as we grow.

This is a hands-on role on a team that runs today, and scale is the focus. You will manage quality and capacity, build the processes, tools, and automation that let the team handle more volume without losing quality, and use data to make decisions as volume grows.

Responsibilities

• Lead the existing team
• Manage When’s full-time licensed agents, including scheduling, coaching, and performance management.
• Own the member experience across phone, email, and chat, including outreach cadence, scripts, escalation paths, and enrollment workflows.
• Run quality assurance and training: call and email review, scorecards, calibration, and onboarding for every agent, internal or contracted.
• Serve as the escalation point on complex member situations, providing guidance and judgment rather than taking the queue.
• Lead and continuously improve the Member Services process across technical issues, platform troubleshooting, and non-technical member questions.
• Hire, onboard, and develop agents as the team grows.
• Build out the team as When scales, including specialist roles such as enrollment and licensing. You do not need to be licensed to manage them.
• Own the team’s tools and workflows in Zendesk, and work with Product and Technology on agent tooling, automation, and the digital-to-human handoff.
• Find opportunities to automate and simplify the team’s work, including with AI-assisted tools.
• Forecast capacity against open enrollment, Medicare AEP, January 1 ICHRA effective dates, client launches, and reduction-in-force events.
• Plan and manage capacity across full-time agents, partners, and contractors, and make the case for when to add each.
• Manage the 1099 contract agent network and overflow agency partners, including sourcing, training, ramp, seasonal activation, and performance review.
• Hold partner and contractor agents to the same quality and compliance standard as internal staff, with the monitoring to prove it.
• Own the budget for the team, including contractor and partner spend, and partner with leadership on the capacity and cost model.
• Own the agency KPI framework: speed to answer, abandonment, response time, first-contact resolution, quality, CSAT, productivity, enrollment completion, and COBRA participation rate.
• Turn performance data into operating decisions, and build the dashboards the team and leadership use.
• Supply Customer Success with member engagement and COBRA deflection data on a fixed cadence, and drive that measurement toward product instrumentation rather than manual compilation.
• Partner with leadership on how Member Services scales as volume and products grow.

Qualifications

• 8+ years in customer support or contact center operations, including 4+ years leading teams.
• Strong technical skills: hands-on with Zendesk or a similar platform, workflow automation, and reporting tools, and comfortable using AI-assisted support tools.
• Highly analytical: comfortable defining KPIs, building dashboards, and turning performance data into operating decisions.
• Experience in health care, digital health, health insurance, benefits, or another health-related setting.
• Experience with capacity planning for volume that changes through the year.
• Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team.
• Excellent communication, high emotional intelligence, and the ability to make complex health insurance topics simple.
• Effective in an early-stage environment: strategic when it matters, hands-on by default.

Requirements

• Familiarity with HubSpot and business intelligence tools such as Metabase.
• Experience standing up a quality assurance program from scratch rather than inheriting one.
• Bachelor’s degree or equivalent relevant experience.

Compensation, Location, and Travel

• Competitive salary ($150,000 to $170,000)
• 100% of health insurance paid
• Stock options and more
• Remote role with minimal travel for company and occasional client meetings