NEWCaplight raises a $16M Series A, led by BlackRock and Fin Capital →
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When

When

Private
Chicago, IllinoisEnterprise Softwarehttps://www.forwhen.com/

Last Round

Series A

Jan 30, 2026

Total Funding Raised

$17.2M

Company Overview

When is a software company that provides an AI-powered platform to help employees navigate post-employment transitions, including finding affordable alternatives to COBRA health insurance.

Sector

Enterprise Software

Verticals

HR, InsurTech, Workflow Automation, NLP & Conversational AI

Business Model

B2B

Customer Profile

Subscription SaaS, Services & Consulting, Marketplace Commission

AI Layer

Application

Keywords

workforce transitionsemployee offboardingoffboarding softwareCOBRA administrationCOBRA alternativebenefits navigationHRIS integrationhealth insurance marketplaceoffboarding automationemployee benefits platforminsurtechHR techconversational AIbenefits administrationAI benefits advisor

Historical Pricing

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When Comps

Public and private peers based on sector, stage, and business model.

When comps — public and private peers by sector, stage, and business model
CompanyStatusEst. ValuationRev Multiple
OpenAIPrivate$86.0B~40x
CoherePrivate$5.0B--
Competitor 1Public$XX.XBXXx
Competitor 2Public$XX.XBXXx

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When Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series AJan 30, 2026
SeedAug 1, 2024

Key People

Founding team and executive leadership

Patrick Koeller

CTO

Executive Team

Brett Cable

Chief Financial Officer

Executive Team

When Investors

Notable investors and investment history

When investors
InvestorRounds
Enfield Capital PartnersSeries A, Seed
B Capital GroupSeries A, Seed
7wire VenturesSeries A
Network VenturesSeed
TTV CapitalSeries A, Seed
Joyance PartnersSeed
ManchesterStory GroupSeries A

When Filings

SEC and related filings with document metadata.

Data table
TypedDateAmount OfferedAmount SoldFillingPagesDownload
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When Filings

SEC and related filings with document metadata.

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Firmographic Details

HeadquartersChicago, Illinois
Employee Range28
Year Founded2020
Last FundingJan 30, 2026

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