Director of Member Services & Operations

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

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.