When Insurance
When Insurance is an AI-driven workforce transitions platform that helps self-insured employers reduce COBRA costs and guide departing, retiring, and Medicare-eligible employees to affordable ACA, private, and Medicare coverage via a conversational AI navigator and licensed-broker concierge.
- Company typePrivate
- Founded2020
- HeadquartersHighwood, United States
- Headcount11–50
- GTM typeB2B
- OfferingSoftware
What When Insurance does
When Insurance Agency, Inc. (operating as "When") is an AI-driven workforce transitions platform that helps self-insured employers reduce COBRA-related claims costs while guiding departing employees to affordable ACA, private, and Medicare coverage. Founded in 2020 by Andy Hamilton (former Expedia Group / ApartmentJet) and Dan Wertheimer (former Target Senior Director of Innovation), the company is headquartered in Chicago, Illinois, with a registered office in Highwood, IL. Its core technology is the Jamie AI plan navigator — a conversational assistant that performs intelligent plan matching, subsidy optimization, and in-network verification — wrapped around a licensed-broker concierge service. The platform integrates with major HRIS systems (Workday, Paychex, Paycom, HiBob, Paylocity) via API or secure file transfer and is typically deployed in 2-4 weeks without disrupting existing COBRA processes, carriers, or plan designs.
The product portfolio is anchored by three interlocking modules: the AI-Powered Health Insurance Marketplace (Jamie), The When Benefit® (an employer-funded health-insurance reimbursement that redirects severance dollars away from COBRA), and Concierge Advisor Support staffed by licensed, salaried (non-commissioned) advisors appointed with Cigna, UnitedHealthcare, Aetna, and Blue Cross Blue Shield. Two purpose-built add-ons sit on top: Medicare Navigation Services (HRIS-triggered proactive outreach to employees approaching age 65) and a life-event solution suite for involuntary exits, voluntary exits, retirement, and dependent transitions. When is licensed as an independent insurance broker and operates in all 50 U.S. states.
The business model combines three revenue streams: (1) insurance broker commissions from third-party carriers when departing employees enroll in marketplace, Medicare, or other coverage through the platform; (2) enterprise SaaS/platform subscription fees paid by self-insured employers on typically multi-year contracts; and (3) carrier/TPA embed fees where When is rolled into an ASO structure, fully insured premium, or stop-loss arrangement. Distribution is omnichannel: direct enterprise sales to Fortune 50/500 self-insured employers, a flagship reseller agreement with national COBRA administrator P&A Group, channel partnerships with TPAs/PEOs/ASOs, broker and captive-insurance channels, and a self-serve employee portal. As of January 2026, the company reported 6,200+ customer companies, 1M+ eligible employees, 75,000 employee life-events cases managed, $5M+ in cash benefits managed through The When Benefit®, 4X year-over-year revenue growth, and a board that includes newly appointed HR-tech leader Tara Conger. Total disclosed funding is $14.8M across a $4.6M seed (B Capital, August 2024) and a $10.2M Series A (ManchesterStory and 7wire Ventures co-led, January 2026).
When Insurance firmographics
Firmographics- Name
- When Insurance
- Legal name
- When Insurance Agency, Inc.
- Website
- https://forwhen.com
- Company type
- Private
- Founded year
- 2020
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- When Insurance is an AI-driven workforce transitions platform that helps self-insured employers reduce COBRA costs and guide departing, retiring, and Medicare-eligible employees to affordable ACA, private, and Medicare coverage via a conversational AI navigator and licensed-broker concierge.
- Ownership category
- akta.pro rank
When Insurance industry classification
Industry- Product category
- Employee Benefits Technology (Health Insurance Transition Platform)
- NAICS
- Insurance Agencies and Brokerages (52421), Pharmacy Benefit Management and Other Third Party Administration of Insurance and Pension Funds (524292), Agencies, Brokerages, and Other Insurance Related Activities (5242)
- SIC
- Insurance Agents, Brokers & Service (6411), Services-Prepackaged Software (7372), Services-Computer Integrated Systems Design (7373)
- akta.pro primary industry
- COBRA & Retiree Continuation Administration (HLAEAAAJ)
- akta.pro secondary industries
- Employer Health Reimbursement Arrangements (HRA/ICHRA/QSEHRA) Administration (HLAEAAAG), Self-Funded (ASO) Group Health Plans & Stop-Loss (FSAIAFAB), Employer/Member Engagement Platforms for Provider-Sponsored Plans (HLACAEAM)
Keywords
Where When Insurance is headquartered
LocationHeadquarters
- HQ city
- Highwood
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
When Insurance business model
Business model- GTM type
- B2B
- Offering type
- Software
- Cost components
- Technology or R&D, Personnel, Marketing or Sales, Operations, Others
Revenue model
- Insurance Broker Commissions: When operates as a licensed independent insurance broker / Healthcare.gov partner and receives commissions from third-party health insurance providers when departing employees enroll in marketplace, Medicare, or other coverage through the platform. Commission amounts vary by carrier and product; liability cap in ToS is tied to commissions received per user.
- Employer SaaS Subscription / Platform Fees: Self-funded employers pay for access to the When workforce transitions platform (When Benefit®, AI marketplace, concierge support, HRIS integration, COBRA Savings Calculator). Pricing is enterprise / quote-based rather than publicly disclosed, typically multi-year contracts.
- Carrier / TPA Embed Fees: When can be embedded inside a carrier's ASO fee structure or fully insured premium, allowing the partner to roll the When service into its existing offering and earn share-of-savings economics on COBRA claims reduction.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Other | Multi-year contract | Enterprise / Employer contract — quote-based, not publicly listed |
| Other | Multi-year contract | Channel / Reseller — embedded into partner pricing |
Go-to-market motion3 records
Distribution channels8 records
Marketing channels8 records
When Insurance product offering
Product offeringCore offering
When Insurance operates an AI-powered workforce transitions platform that helps self-insured employers reduce COBRA-related claims costs by up to 80% by guiding departing employees to personalized ACA, private, and Medicare coverage. The platform combines a conversational AI plan navigator ("Jamie"), employer-funded health reimbursement (The When Benefit®), licensed-advisor concierge support, Medicare navigation services, and HRIS-native integrations (Workday, Paychex, Paycom, HiBob, Paylocity) deployed in 2–4 weeks. It monetizes via employer SaaS subscription fees and commissions from third-party health insurance carriers when employees enroll.
Product overview
When Insurance operates a single unified AI-powered workforce transitions platform ("When Platform") augmented by a small set of named modules and tools. The core Platform consists of three interlocking modules: the AI-Powered Health Insurance Marketplace (Jamie, the conversational plan navigator), the When Benefit® (employer-funded healthcare reimbursement acting as a smart COBRA alternative), and the Concierge Advisor Support team (salaried licensed advisors). Two purpose-built add-ons sit on top of the platform: Medicare Navigation Services (education hub, licensed advisors, webinars, proactive HRIS-triggered outreach to employees approaching 65) and When Solutions (tailored life-event packages for involuntary exits, voluntary exits, retirement, dependents, restructuring, and temporary staff). A public-facing COBRA Savings Calculator rounds out the portfolio as a demand-generation and customer-modeling tool.
Differentiator
Problem solved
Functional benefit
Brands
- The When Benefit®: A smart COBRA alternative employer-funded health insurance reimbursement solution offered through When's platform. Replaces costly COBRA subsidies, lump sum cash, and continuation coverage.
- Jamie
Products and services
- When Platform (AI Workforce Transitions Platform) Unified AI-powered platform that turns workforce change into savings by lowering high-cost medical claims, reducing COBRA liability, and protecting employer brand during employee transitions. Integrates with major HRIS systems to trigger personalized offboarding workflows. Sold to self-insured enterprise employers.
- The When Benefit® Employer-funded health insurance reimbursement solution that replaces costly COBRA subsidies, lump-sum cash, and continuation coverage. Functions as smart severance for involuntary exits, early-retirement bridge, COBRA migration, and ICHRA reimbursement for current employees.
- Medicare Navigation Services Medicare education hub, licensed Medicare advisor consultations (1:1), customized webinars, and enrollment support for active employees approaching 65, retiring employees, and dependents. Proactively identifies eligible employees via HRIS data and serves them across all 50 states.
- COBRA Savings Calculator Interactive public calculator that estimates employer savings from reducing COBRA elections by redirecting departing employees to ACA marketplace alternatives. Used as demand-generation and customer-modeling tool driving Schedule a Demo conversions.
Companies that use When Insurance
Customer profileNamed customers2 records
Ideal customer profiles3 records
When Insurance technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- Yes
- API docs
- API detail
Core technology
AI maturity
App detail
Integration6 records
AI capability2 records
Feature6 records
When Insurance partnerships and signals
Strategic signalPartnerships
13 partnerships are on record, tiered flagship commercial partner, minor (segment-expansion partnership), minor (individual advisor), core technology integration, core integration and core carrier relationship.
- P&A Groupflagship commercial partnerStrategic reseller partnership announced April 8, 2026. P&A Group (a national third-party benefits administrator for 50 years, based in Williamsville, NY, specializing in COBRA, FSA, HRA, HSA, and billing) resells When's healthcare transition solutions to its employer clients nationwide. P&A Group positions When as an extension of its existing COBRA administration services, helping clients reduce COBRA-related costs while providing departing employees with personalized, affordable coverage alternatives.
- Iowa State Universityminor (segment-expansion partnership)When Partners with Iowa State University (Apr 22, 2025) to help graduating students navigate health insurance as they transition out of student health plans — a partnership that expands When's reach into higher education.
- Tara Congerminor (individual advisor)Joined When's Board of Directors in December 2024 (per 'When Welcomes Tara Conger to Board of Directors' announcement). Listed here as a governance relationship rather than a customer or investor.
- Quotit Corporationcore technology integrationQuotit Corporation provides health insurance plan information ('Quotit Information') surfaced through the When Service. Subject to a separate end-user license agreement; used by When to source ACA marketplace plan data for departing employees.
- Workdaycore integrationPre-built HRIS integration enabling When to receive employee case files, identify employees approaching Medicare eligibility, and trigger offboarding workflows via API or secure file transfer. Supports 180° / 360° data flows; implementation completed in 2-4 weeks.
- Paychexcore integrationPre-built HRIS integration enabling When to receive employee case files and trigger offboarding workflows. Listed alongside Workday on the Platform page as a supported HRIS system.
- Paycomcore integrationSupported HRIS system — When connects via API or secure file transfer to identify employees leaving and employees approaching Medicare age (referenced in Brook West's 'easiest cost-containment solution' blog post).
- HiBobcore integrationSupported HRIS system — When connects via API or secure file transfer to identify employees leaving and employees approaching Medicare age.
- Paylocitycore integrationSupported HRIS system — When connects via API or secure file transfer to identify employees leaving and employees approaching Medicare age.
- Cignacore carrier relationshipWhen's licensed advisors are appointed with Cigna (alongside UHC, Aetna, Blue Cross Blue Shield) so they can pull up actual plans, compare them side-by-side, and enroll members directly. Carrier appointments are handled by When, with no regulatory burden pushed to the employer health plan.
- UnitedHealthcare (UHC)core carrier relationshipWhen's licensed advisors are appointed with UnitedHealthcare (UHC) alongside Cigna, Aetna, and Blue Cross Blue Shield — enabling direct plan comparison, quoting, and enrollment.
- Aetnacore carrier relationshipWhen's licensed advisors are appointed with Aetna (alongside Cigna, UHC, Blue Cross Blue Shield), enabling direct plan comparison and enrollment for departing employees.
- Blue Cross Blue Shieldcore carrier relationshipWhen's licensed advisors are appointed with Blue Cross Blue Shield (alongside Cigna, UHC, Aetna), enabling direct plan comparison and enrollment for departing employees.
Scale indicators14 records
Recent moves6 records
Expansion highlights6 records
When Insurance competitors and assessment
Company assessmentDirect peers
- Take Command Health: Take Command is an ICHRA administration and COBRA-alternative platform that helps employers offer personalized, portable health coverage to departing employees via licensed advisors — directly overlapping with When's core AI-powered marketplace, concierge support, and HRA-style reimbursement products.
- P&A Group: P&A Group is a national COBRA, FSA, HRA, and HSA third-party benefits administrator that is now a strategic reseller of When — a meaningful peer because it competes in COBRA administration services and is also When's flagship distribution partner.
- PeopleKeep (by Bennie): PeopleKeep is a dedicated ICHRA administration platform for small and mid-sized employers, offering personalized plan recommendations and a concierge-style advisor experience that closely mirrors When Benefit® and the Jamie plan navigator.
Broad incumbents
- Mercer (Marsh McLennan): Mercer is a global benefits consulting and brokerage firm advising the same Fortune 500/HR leaders that When targets — overlapping as both a potential channel partner and a competitor that could build or white-label a comparable AI workforce transitions solution.
- Aon (Health & Benefits): Aon's Health & Benefits practice is a major benefits broker and consultant for large self-funded employers, overlapping with When's target buyer and increasingly incorporating technology-enabled solutions that could compete with or complement the When platform.
- HealthEquity: HealthEquity is a leading HSA and consumer-directed benefits platform that increasingly competes in HRA, COBRA, and employer benefit-administration adjacencies — a broad incumbent with overlapping use cases for departing employees.
- WEX Health: WEX Health is a large incumbent benefits-administration platform for HSA, HRA, FSA, COBRA, and consumer-directed healthcare — overlapping with When's HRA/COBRA-alternative offering and serving the same self-funded employer buyer.
- ADP (Benefits/PEO): ADP's benefits administration, PEO, and HRIS offerings serve the same self-funded employer market as When and could bundle COBRA-alternative functionality into its existing platform, posing both a partnership and competitive threat.
Emerging players
- Thatch: Thatch is an emerging ICHRA and health-benefits fintech that uses technology to help employers fund personalized health coverage for employees — overlapping with When's When Benefit® reimbursement product and AI-driven plan matching approach.
- Remodel Health: Remodel Health is an emerging ICHRA-focused platform that helps employers transition from group health plans to defined-contribution models — directly competing with When's HRA/ICHRA use case and COBRA-alternative positioning.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat6 records
Key risks7 records
Key highlights7 records
Customer concentration
When Insurance social profiles
Digital presenceWhen Insurance compliance and trust
Trust signalCompliance4 records
When Insurance financial estimates
Financial estimateRevenue estimate
Valuation estimate
When Insurance leadership team
Management profileNumber of profiles
Profiles7 records
When Insurance funding detail
Funding detailFunding overview
Funding rounds5 records
Investors10 records
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
When Insurance M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about When Insurance
What does When Insurance do?
When Insurance operates an AI-powered workforce transitions platform that helps self-insured employers reduce COBRA-related claims costs by up to 80% by guiding departing employees to personalized ACA, private, and Medicare coverage. The platform combines a conversational AI plan navigator ("Jamie"), employer-funded health reimbursement (The When Benefit®), licensed-advisor concierge support, Medicare navigation services, and HRIS-native integrations (Workday, Paychex, Paycom, HiBob, Paylocity) deployed in 2–4 weeks. It monetizes via employer SaaS subscription fees and commissions from third-party health insurance carriers when employees enroll.
Is When Insurance a public or private company?
When Insurance is a private company. It is classified as venture growth investor backed and is currently operating.
When was When Insurance founded?
When Insurance was founded in 2020. It employs 11 to 50 people.
Where is When Insurance based?
When Insurance is headquartered in Highwood, United States, in the North America region.
How does When Insurance make money?
Three revenue lines are on record. Insurance Broker Commissions are the primary driver. The others are employer SaaS Subscription / Platform Fees and carrier / TPA Embed Fees.
Who are When Insurance's main competitors?
Direct peers on record are Take Command Health, P&A Group and PeopleKeep (by Bennie). Broad incumbents are Mercer (Marsh McLennan), Aon (Health & Benefits), HealthEquity, WEX Health and ADP (Benefits/PEO). Emerging players are Thatch and Remodel Health.
Does When Insurance have an API?
Yes. When offers an HRIS-facing API used to securely synchronize employer eligibility and qualifying-event data into the When platform. The platform supports 180° and 360° data flows via CSV or API for inbound employee data (departures, Medicare eligibility triggers). API is used by HR systems (Workday, Paychex, Paycom, HiBob, Paylocity) and channel partners (TPAs, PEOs, COBRA administrators). No public developer-facing documentation portal is exposed; integration is implemented through partner onboarding with When's team. Implementation typically completes in 2-4 weeks.
What industry is When Insurance in?
When Insurance's product category is Employee Benefits Technology (Health Insurance Transition Platform). Its primary akta.pro industry code is HLAEAAAJ, COBRA & Retiree Continuation Administration, with a secondary code of HLAEAAAG, Employer Health Reimbursement Arrangements (HRA/ICHRA/QSEHRA) Administration. Its NAICS code is 52421 and its SIC code is 6411.