Director, Member Services Operations (Fully Remote)

When; United States; Remote; USD 120,000 - 180,000; Full time

Job summary

When is seeking an operations leader to manage our full-time licensed agents and own the member experience across phone, email, and chat. You will oversee scheduling, coaching, and performance management, driving QA, training, and enrollment workflows.

You will collaborate with Product and Technology to optimize Zendesk tooling, automation, and AI-assisted handoffs, while forecasting capacity and managing the 1099 network and partner agencies. This role reports to executive leadership.

Qualifications

• Experience leading licensed agent teams and driving onboarding.
• Proven ability to design and improve member experiences.
• Strong coaching, QA, and training capabilities.
• A track record of building and using KPI dashboards.

Responsibilities

• Manage full-time licensed agents: scheduling, coaching, performance management.
• Own member experience across phone, email, and chat with outreach cadences and enrollment workflows.
• Run QA and training: call/email review, scorecards, calibration, onboarding.
• Own tools/workflows in Zendesk; collaborate with Product/Tech on tooling and automation.
• Identify opportunities to automate with AI-assisted tools.
• Forecast capacity across enrollment events and contractor network.
• Manage 1099 agents and overflow agency partners.
• Own agency KPI framework and dashboards for leadership; provide performance data.
• Deliver engagement and COBRA data to Customer Success.

Skills

Team management

Coaching

Performance management

Customer success

Data analysis

KPI dashboards

Tools

Zendesk

Job description

• 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

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.