
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.
🔥 5 minutes ago
🐊 Florida, Iowa, +4 more states – Remote
💵 $70k - $80k / year
⏰ Full Time
🟢 Junior
🟡 Mid-level
🔒 Insurance
👻 Ghost score 0%
Where this job comes from
Posted on When's careers page, not through a job board
First seen by Remote Rocketship 5 minutes ago

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.
• Conduct needs assessments and present plan and enrollment options across ACA Marketplace and Medicare product lines • Handle inbound phone contacts from individuals navigating a loss-of-coverage Special Enrollment Period or annual enrollment window • Determine eligibility for ACA Marketplace plans, Medicare Advantage, Medicare Supplement, or Part D coverage • Clearly present and compare benefits, premiums, deductibles, and network considerations • Document interactions and enrollment outcomes in the designated CRM platform • Meet or exceed individual service level, quality, and productivity metrics • Maintain active licensure in all required states throughout the engagement • Stay current on plan offerings, carrier guidelines, CMS regulations, and SEP eligibility rules • Collaborate with non-licensed support staff receiving warm transfers and handing off pre-qualified contacts • Work during call-center hours of 9am to 6pm CT, Monday through Friday
• Active health insurance producer license in good standing, with a resident license in Iowa, Minnesota, Washington, Oregon, South Carolina, or Florida • Not currently captive with another insurance agency or carrier • Minimum 2 years of experience selling individual health insurance, ACA Marketplace plans, or Medicare products • Demonstrated experience conducting enrollment conversations via phone • Strong working knowledge of ACA subsidy calculations, SEP qualifying events, and Medicare eligibility rules • Ability to work independently in a remote environment with minimal supervision • Reliable high-speed internet connection and a quiet, dedicated workspace • Proficiency with CRM tools and web-based enrollment platforms • Active licensure in multiple states preferred • Experience in a high-volume inbound call center environment preferred • AHIP Medicare certification (current year preferred) • Bilingual (English/Spanish) a plus • Candidates must be authorized to work in the United States • Licensure verification prior to contract execution
• Equity • Remote work arrangement
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