
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.
🔥 1 minute ago
Where this job comes from
Posted on When's careers page, not through a job board
First seen by Remote Rocketship 1 minute 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.
• Design, build, and run multi-channel outreach programs across email, SMS, direct mail, print, and digital channels • Own the When Medicare 64½ outreach journey from proactive education through engagement • Own the When Choice separation journey during the election window • Build segmentation and cadence logic based on election deadlines, Medicare enrollment windows, and plan year dates • Own engagement and enrollment KPIs and report weekly on performance and drivers • Run continuous testing of creative, subject lines, channel mix, send timing, and offer framing • Partner with licensed agents to improve the handoff from outreach to one-on-one guidance and identify member drop-off points • Improve landing page and inbound flow conversion with design and product teams • Build co-branded client engagement playbooks, HR toolkits, manager talk tracks, and internal communications templates • Work with Customer Success on launch communications and engagement lift plans for underperforming accounts • Tailor programs for self-insured employers, Medicare-eligible active populations, and broker-sold ICHRA groups • Write and manage clear, plain-language, compliant member-facing copy • Route Medicare and insurance-facing copy through compliance review • Maintain accessibility and readability standards across member-facing assets • Own the marketing automation and campaign stack for member engagement • Maintain clean, auditable data flows between eligibility files, CRM, and outreach tools • Build trusted leadership dashboards
• 5+ years in lifecycle, growth, or engagement marketing with direct ownership of conversion metrics • Demonstrated experience running multi-channel campaigns at scale, with six figures of contacts or more and documented lift • Hands-on experience with marketing automation and CRM platforms such as HubSpot, Marketo, Braze, Iterable, or similar • Ability to build campaigns directly rather than only briefing them out • Strong plain-language writing skills for complex, high-stakes topics • Analytical fluency in segmentation, funnel analysis, test design, and defending results • Healthcare, health insurance, benefits, or regulated-industry marketing experience strongly preferred • Familiarity with COBRA, ACA, Medicare, or ICHRA mechanics, or ability to learn a complex regulatory domain quickly, strongly preferred • Experience marketing to populations reached through employer or partner channels preferred • Experience working alongside a licensed sales or agent team preferred • Experience with Klaviyo and Claude is a plus • Must be currently authorized to work in the United States • Must not require sponsorship for employment authorization now or in the future
• 100% employer-paid health insurance • Stock options • Minimal travel for company meetings and occasional client meetings • Remote work arrangement
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