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§ Private Profile · 39 Pralls Loop, Highwood, Illinois, 60040, United States
AI-driven off-boarding platform simplifying health insurance transitions.
When Insurance develops an AI-powered workforce transitions platform designed for employers to manage employee life events and associated benefits. The platform leverages artificial intelligence to guide departing employees toward affordable health coverage alternatives, actively reducing high-cost medical claims and mitigating COBRA liabilities. This solution integrates an AI-driven marketplace with concierge advisor support, streamlining complex transitions for human resources teams while ensuring comprehensive employee well-being.
The company's inception dates back to the Great Recession of 2008, when co-founder Dan Wertheimer conceived the foundational idea as a business school project. Alongside co-founder Andy Hamilton, they established When Insurance to address the critical need for improved health benefits solutions during workforce changes, moving beyond traditional COBRA options. Their insight centered on transforming potentially costly and negative employee exits into a more supportive and financially prudent experience for both parties.
When Insurance primarily serves employers, aiming to provide a better outcome for all stakeholders involved in workforce transitions. The company's vision is to redefine how organizations handle employee departures by offering a platform that not only reduces healthcare costs and financial risks but also strengthens employer branding. They strive to simplify complex processes, ensuring employees feel supported and guided through crucial life events, fostering continued brand loyalty.
When Insurance has raised $15.2M across 2 funding rounds.
When Insurance has raised $15.2M in total across 2 funding rounds.
When Insurance has raised $15.2M across 2 funding rounds. Most recently, it raised $10.2M Series A in January 2026.
| Date | Round | Lead Investors | Other Investors | Status |
|---|---|---|---|---|
| Jan 30, 2026 | $10.2M Series A | 7wire Ventures, Manchesterstory Group, Nicole Gunderson | Alumni Ventures, B Capital, Enfield Capital Partners, Mairs & Power Venture Capital, TTV Capital, Bascom Ventures | Announced |
| Jul 1, 2024 | $5M Seed | B Capital Group | Alumni Ventures, Felicis Ventures, Modern Venture Partners, Greg Papadopoulos, Jeff Immelt, Norwest Venture Partners, XYZ Venture Capital, Bascom Ventures, Enfield Capital Partners, Joyance Partners, Network Ventures, Lizzie Guynn | Announced |
When Insurance is an insurtech company specializing in parametric insurance solutions, using technology like AI and event-triggered policies to provide rapid payouts for climate-related risks such as rainfall and floods.[1] Launched in 2023, it targets underserved markets where traditional insurance falls short, serving individuals and businesses in high-risk areas by automating claims via predefined triggers rather than lengthy assessments, thus solving the protection gap with faster, transparent coverage.[1] The company has gained early momentum amid rising climate disasters, positioning itself as a nimble player in a sector projected to grow through AI-driven personalization and efficiency gains.[1][7]
When Insurance emerged in 2023 as a response to escalating climate risks, with founders leveraging insurtech trends like parametric models to address gaps in conventional coverage.[1] While specific founder backgrounds are not detailed in available sources, the company's inception aligns with the broader insurtech wave starting around 2010, building on technologies such as big data, AI, and blockchain to automate insurance processes.[5] Early traction came from focusing on event-triggered policies for rainfall and flood events, capitalizing on pivotal moments like increasing natural disasters that traditional insurers struggle to cover affordably.[1]
When Insurance rides the insurtech wave transforming the $6 trillion insurance industry through AI, IoT, and parametric innovations, particularly as climate change widens protection gaps.[1][5][7] Its 2023 timing is ideal, coinciding with surging cyber threats, wellness tech integration, and generative AI trends projected to dominate 2025 by optimizing underwriting and personalization.[1][7] Market forces like consumer demand for seamless digital experiences and regulatory pushes for efficiency favor startups like When Insurance, which collaborate with carriers to quantify risks and prevent losses.[5] It influences the ecosystem by accelerating parametric adoption, pressuring incumbents to modernize and fostering a hybrid model of tech startups and traditional players.[3][5]
When Insurance is poised for expansion as parametric insurance scales with climate volatility and AI advancements, potentially partnering with larger carriers for broader distribution.[1][5][7] Trends like generative AI for tailored pricing and IoT for real-time risk data will shape its trajectory, enabling deeper market penetration despite challenges like regulation and data privacy.[2][7] Its influence may evolve from niche disruptor to ecosystem enabler, driving industry-wide efficiency while addressing global risks—reinforcing insurtech's role in making insurance more accessible and resilient.[1][6]
When Insurance has raised $15.2M in total across 2 funding rounds.
When Insurance's investors include 7wire Ventures, ManchesterStory Group, Nicole Gunderson, Alumni Ventures, B Capital, Enfield Capital Partners, Mairs & Power Venture Capital, TTV Capital, B Capital Group, Felicis Ventures, Modern Venture Partners, Greg Papadopoulos.