Director, Member Services Operations; Fully Remote

• 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.

Tools, Data, and Automation:

• 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.

Capacity and Contractor Management:

• 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.
• Manage the 1099 contract agent network and overflow agency partners.

Performance and Reporting:

• 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.

When provides an enterprise platform for guided health insurance decisions at qualifying life events, combining intelligent decision-support with licensed agents. We have supported over one million employees and managed over 204,000 qualifying events, maintaining a lean, hands-on team focused on quality and scale.