Head of Insurance Operations

🔥 5 minutes ago

🇺🇸 United States – Remote

💵 $150k - $170k / year

⏰ Full Time

🔴 Lead

⚙️ Operations

👻 Ghost score 0%

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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 full-time licensed agents through scheduling, coaching, and performance management • Own member support across phone, email, and chat, including outreach cadence, scripts, escalation paths, and enrollment workflows • Run quality assurance and training through call and email review, scorecards, calibration, and onboarding • Serve as escalation point for complex member situations • Improve member support processes for technical issues, platform troubleshooting, and non-technical questions • Own hiring strategy and sequencing for the Agency function • Recruit and develop the agency team and identify capacity, planning, and enrollment gaps • Decide between internal, partner, and contractor capacity based on cost, quality, and risk • Manage overflow agency partners, including scope, commercial terms, onboarding, service levels, escalations, and performance review • Build and manage the 1099 contract agent network, including sourcing, licensing verification, training, ramp, and seasonal activation • Forecast capacity for open enrollment, Medicare AEP, ICHRA effective dates, client launches, and reduction-in-force events • Maintain 50-state licensure, renewals, continuing education, agent certifications, and carrier appointments • Ensure compliance with CMS Medicare marketing requirements, state producer conduct rules, ACA and ICHRA requirements, and privacy obligations • Own agency KPIs, client service-level commitments, response-time reporting, enrollment and commission tracking, reconciliation, and revenue forecasting • Supply Customer Success with member engagement and COBRA deflection data • Partner with Customer Success, Product, Technology, and Finance on onboarding, service levels, tooling, CRM workflows, automation, member support costs, commissions, and reimbursement workflows • Report to When’s Co-Founder and build a management layer beneath the role

🎯 Requirements

• 10+ years in licensed insurance service operations, with at least 5 years leading teams • Health insurance producer licensure held currently or previously • Experience scaling a licensed contact center through multiple Medicare AEP or ACA open enrollment cycles • Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team • Working fluency in Medicare marketing and compliance rules and in ACA individual market and ICHRA enrollment mechanics • Familiarity with agency licensing and carrier appointment operations, including NIPR or Sircon workflows • Ability to define KPIs, build dashboards, and turn performance data into operating decisions • Experience hiring into a function being built, including writing the role, making the case, and ramping the person • Excellent communication and high emotional intelligence • Ability to make complex health insurance topics simple • Ability to operate strategically and hands-on in an early-stage environment • Strongly preferred: background at an FMO, BGA, carrier direct-to-consumer or individual market service organization, or a licensed agency operating at national scale • Strongly preferred: experience with coverage transitions, COBRA or Medicare, qualifying life events, or employee benefits administration • Strongly preferred: familiarity with Zendesk, HubSpot, and business intelligence tools such as Metabase • Strongly preferred: experience standing up a quality assurance program from scratch • Strongly preferred: Bachelor’s degree or equivalent relevant experience • Must be authorized to work in the United States or otherwise address U.S. employment authorization requirements

🏖️ Benefits

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

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