Protecting your family's health and financial wellness when you need it most.
Location: United States, Illinois, Highwood
Employees: 1-10
Total raised: $14.6M
Investors 4
| Date | Name | Website |
| - | B Capital ... | b.capital/ |
| - | B Capital ... | bcapgroup.... |
| 22.12.2025 | Mairs &... | mairsandpo... |
| 09.08.2022 | Network Ve... | networkven... |
Funding Rounds 2
| Date | Series | Amount | Investors |
| 30.01.2026 | Series A | $10M | - |
| 01.08.2024 | Seed | $4.6M | - |
Mentions in press and media 8
| Date | Title | Description |
| 26.02.2026 | Amid Aging Workforce and Rising Healthcare Costs, When Launches Cost-Saving Medicare Solutions | When - Medicare support services When’s support services helps retirees, 65+ workers navigate affordable healthcare I could not have done this without the help of When.” — When Medicare support services user CHICAGO, IL, UNITED STATES, Febr... |
| 02.02.2026 | When Raises $10.2M in Series A Funding | When, a Chicago, IL-based provider of a workforce transitions platform, raised $10.2M in Series A funding. The round was led by ManchesterStory and 7wire with participation from new investor Mairs and Power Venture Capital and existing inve... |
| 30.01.2026 | When raises $10M Series A to transform employee health benefits during critical moments | When Cost Savings Calculator Company expands offerings to make insurance flexible & affordable as economic uncertainty, rising healthcare costs disrupt workforce We're long overdue for better models of managing healthcare and benefits t... |
| 01.08.2024 | When Raises $4.6M in Seed Funding | When, a Chicago, IL-based AI-powered offboarding solution designed to help employees navigate post-employment transitions and maintain access to healthcare by offering more affordable alternatives to COBRA, closed its latest Seed funding ro... |
| 11.09.2016 | Weekend Box Office: 'When The Bough Breaks' Snags $15M Bow, 'Disappointments Room' Disappears | |
| - | When Insurance | “When is the AI offboarding platform that turns layoffs into savings. We reduce COBRA liability by 80%, lower high-cost medical claims, streamline Medicare transitions, and protect your brand with exceptional employee offboarding during RIF... |
| - | When Insurance | “Employee benefits matter even during challenging economic conditions. The When financial wellness benefit keeps health insurance affordable during layoffs, and for employers When and Jamie are a cost saving COBRA alternative.” |
| - | When Insurance | “Discover cost-effective cobra health insurance alternatives for organizations seeking to minimize COBRA expenses and AI offboarding solutions.” |