Head of Insurance Operations

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

📋 Description

• Guide When’s full-time licensed agents through scheduling, coaching, and performance management.

• Oversee member support via phone, email, and chat, which includes outreach cadence, scripts, escalation paths, and enrollment workflows.

• Conduct quality assurance and training through reviewing calls and emails, utilizing scorecards, calibrations, and onboarding processes.

• Act as an escalation point for intricate member situations.

• Enhance member support processes for technical issues, platform troubleshooting, and non-technical inquiries.

• Develop and implement the hiring strategy and sequencing for the Agency function.

• Recruit and cultivate the agency team while identifying capacity, planning, and enrollment deficiencies.

• Make decisions on internal, partner, and contractor capacity based on cost, quality, and risk factors.

• Manage overflow agency partners, encompassing scope, commercial terms, onboarding, service levels, escalations, and performance evaluations.

• Establish and manage the 1099 contract agent network, including sourcing, verifying licenses, training, ramping, and seasonal activation.

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

• Maintain 50-state licensure, including renewals, continuing education, agent certifications, and carrier appointments.

• Ensure adherence to CMS Medicare marketing requirements, state producer conduct regulations, ACA and ICHRA requirements, and privacy obligations.

• Manage agency KPIs, client service-level commitments, response-time reporting, enrollment and commission tracking, reconciliation, and revenue forecasting.

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

• Collaborate with Customer Success, Product, Technology, and Finance on onboarding, service levels, tooling, CRM workflows, automation, member support costs, commissions, and reimbursement workflows.

• Report directly to When’s Co-Founder and establish a management layer beneath this position.

⛳️ Requirements

• 10+ years of experience in licensed insurance service operations, with a minimum of 5 years in a leadership role.

• Current or previously held health insurance producer licensure.

• Proven experience in scaling a licensed contact center through several Medicare AEP or ACA open enrollment cycles.

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

• Proficiency in Medicare marketing and compliance regulations, as well as ACA individual market and ICHRA enrollment processes.

• Familiarity with agency licensing and carrier appointment operations, including NIPR or Sircon workflows.

• Ability to define KPIs, create dashboards, and translate performance data into operational decisions.

• Experience in recruiting for a newly established function, including defining the role, justifying the hire, and onboarding the individual.

• Exceptional communication skills and high emotional intelligence.

• Capability to simplify complex health insurance topics.

• Ability to operate both strategically and hands-on in an early-stage environment.

• Strongly preferred: background in FMO, BGA, carrier direct-to-consumer, individual market service organization, or a licensed agency operating at a 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 like Metabase.

• Strongly preferred: experience in establishing a quality assurance program from the ground up.

• Strongly preferred: Bachelor’s degree or equivalent relevant experience.

• Must be authorized to work in the United States or fulfill U.S. employment authorization requirements.

🏝️ Benefits

• 100% employer-covered health insurance.

• Stock options.

• Minimal travel required for company and occasional client meetings.

• Remote work opportunity.