Director, Member Services Operations

Job not on LinkedIn

🔥 4 minutes ago

🇺🇸 United States – Remote

💵 $150k - $170k / year

⏰ Full Time

🔴 Lead

⚙️ Operations

👻 Ghost score 5%

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When

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2020

🛡️ Insurance

👥 HR Tech

☁️ SaaS

🔥 Funding within the last year

💰 $10.2M Series A on 2026-02

Insurance • HR Tech • SaaS

When is an enterprise platform (When Insurance Agency, Inc. ) that helps employers manage health coverage transitions at qualifying life events. The company provides decision support and guided enrollment for departing employees and other coverage changes—covering COBRA alternatives, Medicare education and enrollment guidance, and broker-aligned ICHRA solutions. When combines technology, licensing, and licensed, non‑commissioned agents to integrate with existing employer benefits workflows, aiming to reduce employer claims exposure and lower renewals. Its products include When Next (decision support), When Medicare Pro (proactive Medicare guidance), and When Choice (ICHRA solution). The platform is positioned for HR and benefits teams at large employers and is licensed in all 50 states.

📋 Description

• Lead When’s Member Services team, including full-time licensed agents and specialists • Manage scheduling, coaching, and performance management • Own the member experience across phone, email, and chat • Define outreach cadence, scripts, escalation paths, and enrollment workflows • Run quality assurance and training through call and email review, scorecards, calibration, and onboarding • Serve as the escalation point for complex member situations • Improve processes for technical issues, platform troubleshooting, and non-technical member questions • Hire, onboard, and develop agents as the team grows • Build specialist roles such as enrollment and licensing • Own team tools and workflows in Zendesk • Partner with Product and Technology on agent tooling, automation, and digital-to-human handoff • Automate and simplify team workflows, including AI-assisted tools • Forecast capacity for open enrollment, Medicare AEP, ICHRA effective dates, client launches, and reduction-in-force events • Manage capacity across full-time agents, partners, and contractors • Manage the 1099 contract agent network and overflow agency partners • Ensure partner and contractor agents meet internal quality and compliance standards • Own the team budget, including contractor and partner spend • Own the agency KPI framework, including speed to answer, abandonment, response time, first-contact resolution, quality, CSAT, productivity, enrollment completion, and COBRA participation rate • Build dashboards and turn performance data into operating decisions • Provide Customer Success with member engagement and COBRA deflection data • Partner with leadership on scaling Member Services as volume and products grow

🎯 Requirements

• 8+ years in customer support or contact center operations • 4+ years leading teams • Hands-on experience with Zendesk or a similar platform • Experience with workflow automation and reporting tools • Comfortable using AI-assisted support tools • Experience 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 seasonally changing volume • Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team • Excellent communication and high emotional intelligence • Ability to make complex health insurance topics simple • Ability to operate effectively in an early-stage environment • Familiarity with HubSpot and business intelligence tools such as Metabase preferred • Experience standing up a quality assurance program from scratch preferred • Bachelor’s degree or equivalent relevant experience preferred • Must be currently authorized to work in the United States • Willingness to work without requiring employment sponsorship

🏖️ Benefits

• 100% employer-paid health insurance • Stock options • Remote work • Minimal travel for company meetings and occasional client meetings

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