W

When

Subscription-based health coverage during job transitions

Overview

ForWhen.com provides a health insurance protection benefit that covers employees’ health insurance premiums during involuntary job loss, offered to employers on a subscription basis. The core product pays the employee’s premiums during transitional periods, while an integrated payroll connection and Jamie offboarding platform help HR teams manage the benefit and exit processes. The company differentiates itself by focusing specifically on maintaining healthcare coverage during job transitions and by pairing the benefit with an offboarding tool, rather than offering broad, generic insurance. Its goal is to help employers boost retention and employee satisfaction by adding financial wellness and healthcare security to their benefits packages.

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About When

Simplify's Rating
Why When is rated
B
Rated B on Competitive Edge
Rated A on Growth Potential
Rated C on Differentiation

Industries

Enterprise SoftwareFinancial ServicesHealthcare

Company Size

11-50

Company Stage

Seed

Total Funding

$6.3M

Headquarters

Highwood, IL

Founded

2020

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What believers are saying

  • When closed a $10.2M Series A on January 30, 2026.
  • Revenue grew 4.3x year over year, signaling strong employer demand.
  • State Farm partnered with When in 2026, validating distribution through major brands.

What critics are saying

  • When depends on employer budgets; downturns and hiring freezes slow subscription growth.
  • COBRA-adjacent competitors and benefits brokers can replicate transition support before 2027.
  • If claims rise faster than pricing, reserve strain can cripple the insurance business.

What makes When unique

  • When monetizes involuntary job loss protection, a niche traditional benefits vendors ignore.
  • When pairs payroll-linked employer coverage with Jamie, its AI offboarding navigator.
  • When launched in 2023 and now supports 6,200+ companies nationwide.

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Funding

Total Funding

$6.3M

Below

Industry Average

Funded Over

3 Rounds

Seed funding is usually the first official round after pre-seed, when a startup has a prototype or concept. It’s typically used to develop the product, test the market, and start building the team. Investors here are often angel investors or early-stage venture capitalists.
Seed Funding Comparison
Above Average

Industry standards

$3.3M
$2M
$2.3M
$3M
$4.6M

Benefits

  • Health Insurance
  • Remote Work Options
  • Stock Options

Growth & Insights and Company News

6 month growth

-13%

1 year growth

-6%

2 year growth

-11%
FinSMEs
Aug 1st, 2024
When raises $4.6M for AI offboarding

When, a Chicago-based AI-powered offboarding solution, raised $4.6 million in Seed funding led by B Capital, with participation from TTV Capital, Joyance Partners, Alumni Ventures, Network Ventures, and Enfield Capital Partners. This brings the total funding to $7 million. The funds will be used to enhance AI capabilities, expand post-employment offerings, and grow the customer base.

Intelligence360 News
Jul 19th, 2024
When Insurance Agency Has Filed A Notice Of An Exempt Offering Of Securities To Raise $4,613,415.00 In New Equity Investment.

When Insurance Agency has filed a notice of an exempt offering of securities to raise $4,613,415.00 in New Equity Investment. When Insurance Agency has filed a notice of an exempt offering of securities to raise $4,613,415.00 in New Equity Investment.According to filings with the U.S. Securities and Exchange Commission, When Insurance Agency is raising up to $4,613,415.00 in new funding. Sources indicate that as part of senior management Chief Executive Officer, Andrew Hamilton played a key role in securing the recent investment and it will aid in aggressively expanding the company, as well as broaden and accelerate product development.About When Insurance AgencyWhen is a novel employee benefit and an offboarding platform built for people first employers. The When Benefit protects an employees ability to pay for health insurance after an involuntary job loss. Our offboarding tool, Jamie, partners with HR Benefit teams to help exiting employees find affordable COBRA alternatives.To learn more about When Insurance Agency, visit http://www.forwhen.com/When Insurance Agency Linkedin Page: https://www.linkedin.com/company/wheninsurance/Contact:Andrew Hamilton, Chief Executive Officer773-320-9545https://www.linkedin.com/in/hamiltonac8/SOURCE: http://www.intelligence360.ioCopyright (c) 2024 SI360 Inc

U.S. Securities and Exchange Commission
Jul 3rd, 2024
SEC FORM D

The Securities and Exchange Commission has not necessarily reviewed the information in this filing and has not determined if it is accurate and complete.The reader should not assume that the information is accurate and complete.

U.S. Securities and Exchange Commission
Oct 10th, 2023
SEC FORM D

The Securities and Exchange Commission has not necessarily reviewed the information in this filing and has not determined if it is accurate and complete.The reader should not assume that the information is accurate and complete.

U.S. Securities and Exchange Commission
Oct 10th, 2023
SEC FORM D

The Securities and Exchange Commission has not necessarily reviewed the information in this filing and has not determined if it is accurate and complete.The reader should not assume that the information is accurate and complete.

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