Director, Member Services Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead the Member Services team at When, which includes full-time licensed agents and specialists.

• Oversee scheduling, coaching, and performance management.

• Take ownership of the member experience across phone, email, and chat channels.

• Establish outreach cadence, scripts, escalation paths, and enrollment workflows.

• Conduct quality assurance and training through call and email reviews, scorecards, calibration, and onboarding processes.

• Act as the escalation point for complex member issues.

• Enhance processes related to technical problems, platform troubleshooting, and non-technical member inquiries.

• Recruit, onboard, and develop agents as the team expands.

• Create specialist positions focused on enrollment and licensing.

• Manage team tools and workflows within Zendesk.

• Collaborate with Product and Technology teams on agent tools, automation, and digital-to-human transitions.

• Streamline and automate team workflows, including the use of AI-assisted tools.

• Forecast capacity for open enrollment periods, Medicare AEP, ICHRA effective dates, client launches, and reduction-in-force events.

• Oversee capacity management across full-time agents, partners, and contractors.

• Manage the network of 1099 contract agents and overflow agency partners.

• Ensure that partner and contractor agents adhere to internal quality and compliance standards.

• Oversee the team budget, including expenditures related to contractors and partners.

• Manage the agency KPI framework, encompassing metrics such as speed to answer, abandonment rates, response times, first-contact resolution, quality, CSAT, productivity, enrollment completion, and COBRA participation rates.

• Develop dashboards and translate performance data into actionable operational decisions.

• Provide Customer Success with data on member engagement and COBRA deflection metrics.

• Collaborate with leadership to scale Member Services in response to increasing volume and product offerings.

⛳️ Requirements

• Over 8 years of experience in customer support or contact center operations.

• More than 4 years of experience in leadership roles.

• Proficient in using Zendesk or a comparable platform.

• Familiarity with workflow automation and reporting tools.

• Comfortable utilizing AI-assisted support tools.

• Proven experience in defining KPIs, creating dashboards, and converting performance data into operational strategies.

• Background in health care, digital health, health insurance, benefits, or a related health sector.

• Experience with capacity planning for fluctuating seasonal volumes.

• Skilled in managing outsourced, partner, or 1099 agent capacity alongside an internal team.

• Exceptional communication skills and high emotional intelligence.

• Ability to simplify complex health insurance topics.

• Capability to function effectively in an early-stage environment.

• Familiarity with HubSpot and business intelligence tools like Metabase is preferred.

• Experience in establishing a quality assurance program from the ground up is preferred.

• A Bachelor’s degree or equivalent relevant experience is preferred.

• Must currently be authorized to work in the United States.

• Willingness to work without requiring employment sponsorship.

🏝️ Benefits

• 100% employer-sponsored health insurance.

• Stock options.

• Remote work flexibility.

• Minimal travel required for company meetings and occasional client engagements.