# forwhen.com

> AI-optimized mirror of forwhen.com containing 137 pages totalling 60,381 words of clean markdown content, structured data, and semantic HTML. Original source: https://forwhen.com. Last updated: 2026-07-26T09:42:24.486Z.

Each page is available as HTML (with JSON-LD structured data) and Markdown (text-only, ideal for LLMs and RAG).

## Homepage

- [When](/content/support/index.html) (138 words)
- [Trust Center - When](/content/trust/index.html): Trust Centers are the fastest and most transparent way to demonstrate your company's commitment to security (74 words)
- [When Status](/content/status/index.html): Welcome to When's home for real-time and historical data on system performance. (147 words)
- [When: The AI Workforce Transitions Platform for Employers](/content/site-root.html): When turns workforce transitions into savings for employers: lower COBRA costs and high-cost claims while guiding employees through every exit. (438 words)

## Articles & Blog Posts

- [support/hc/en-us/articles/26105179510419/index.html](/content/support/hc/en-us/articles/26105179510419/index.html) (370 words)
- [support/hc/en-us/articles/26105228050323/index.html](/content/support/hc/en-us/articles/26105228050323/index.html) (194 words)
- [support/hc/en-us/articles/26105179463571/index.html](/content/support/hc/en-us/articles/26105179463571/index.html) (54 words)
- [support/hc/en-us/articles/28312990448019/index.html](/content/support/hc/en-us/articles/28312990448019/index.html) (64 words)
- [Why is COBRA so Expensive? – When](/content/support/hc/en-us/articles/28325311583123-why-is-cobra-so-expensive/index.html): Under COBRA, eligible individuals are able to continue their group health insurance benefits through their employers. The reason COBRA... (130 words)
- [Affordable Care Act & Healthcare.Gov – When](/content/support/hc/en-us/sections/28326921378195-affordable-care-act-healthcare-gov/index.html) (48 words)
- [What is the community? – When](/content/support/hc/en-us/community/posts/26105228086547-what-is-the-community/index.html): The Help Center community consists of posts and comments organized by topic. Posts might include tips, feature requests, or questions.... (150 words)
- [Which topics should I add to my community? – When](/content/support/hc/en-us/community/posts/26105228095635-which-topics-should-i-add-to-my-community.html): That depends. If you support several products, you might add a topic for each product. If you have one big product, you might add a topic... (109 words)
- [User profile for Andy Hamilton – When](/content/support/hc/en-us/profiles/26029769212691-andy-hamilton/index.html): Recent activity and contributions by Andy Hamilton (173 words)
- [What states are not on the federal ACA marketplace? – When](/content/support/hc/en-us/articles/28325857040659-what-states-are-not-on-the-federal-aca-marketplace.html): The below states operate their own health insurance marketplace instead of using the federal marketplace. These states are:    State Open... (214 words)
- [How much time do I have to make a decision about electing COBRA? – When](/content/support/hc/en-us/articles/28325418638355-how-much-time-do-i-have-to-make-a-decision-about-electing-cobra.html): Typically, you have 60 days after your health insurance coverage ends to elect COBRA. If you don’t make an election within this 60-day... (62 words)
- [Sign up to When](/content/support/auth/v3/register/index.html) (32 words)
- [Feature a post – When](/content/support/hc/en-us/community/posts/26105228119443-feature-a-post/index.html): Community Managers and moderators can get traction for certain posts by featuring them in a topic in your Help Center community. Learn more (33 words)
- [Who is Eligible for COBRA? – When](/content/support/hc/en-us/articles/28325206647059-who-is-eligible-for-cobra/index.html): Under COBRA, eligible individuals include employees who work for an employer with 20 or more employees and who were previously enrolled... (184 words)
- [Reset your password for When](/content/support/auth/v3/password/forgot/index.html) (29 words)
- [Is COBRA Insurance? – When](/content/support/hc/en-us/articles/28325357055763-is-cobra-insurance/index.html): COBRA is not insurance, but rather a law that provides employees and their dependents the option to continue their group health insurance... (47 words)
- [What are subsidies for health insurance plans? – When](/content/support/hc/en-us/articles/28326172521875-what-are-subsidies-for-health-insurance-plans.html): Subsidies for health insurance plans are financial assistance provided by the government to help individuals and families afford health... (183 words)
- [How do I get reimbursed for my When Benefit? – When](/content/support/hc/en-us/articles/28328045418131-how-do-i-get-reimbursed-for-my-when-benefit.html): Required Proof of Payment In order for a reimbursement request to be approved, you will need proof of payment that includes the following... (122 words)
- [What is COBRA? – When](/content/support/hc/en-us/articles/26105179463571-what-is-cobra/index.html): COBRA is an acronym that stands for the Consolidated Omnibus Budget Reconciliation Act. This is a federal law that provides employees and... (54 words)
- [What is a COBRA administrator? – When](/content/support/hc/en-us/articles/28325584085907-what-is-a-cobra-administrator/index.html): A COBRA administrator is a person or entity responsible for managing the Consolidated Omnibus Budget Reconciliation Act (COBRA) benefits... (78 words)
- [How do I know if I'm eligible for a health insurance subsidy? – When](/content/support/hc/en-us/articles/28326268620819-how-do-i-know-if-i-m-eligible-for-a-health-insurance-subsidy.html): To determine if you are eligible for a health insurance subsidy, you can use the Health Insurance Marketplace's eligibility calculator on... (186 words)
- [COBRA – When](/content/support/hc/en-us/sections/28325009652371-cobra/index.html) (38 words)
- [Does my When Benefit Expire? – When](/content/support/hc/en-us/articles/28328191130003-does-my-when-benefit-expire/index.html): Employees have 90 days from date their When Benefit is released to submit an initial reimbursement request. The When Benefit may not be... (84 words)
- [What is Healthcare.gov? – When](/content/support/hc/en-us/articles/28325800311315-what-is-healthcare-gov/index.html): Healthcare.gov is a government website created to help Americans find and enroll in health insurance plans that are compliant with the... (76 words)
- [What is the ACA? – When](/content/support/hc/en-us/articles/28325727885203-what-is-the-aca/index.html): The Affordable Care Act (ACA), also known as Obamacare, is a comprehensive healthcare reform law that was enacted in 2010 under President... (94 words)
- [Which topics should I add to my community? – When](/content/support/hc/en-us/community/posts/26105228095635/index.html): That depends. If you support several products, you might add a topic for each product. If you have one big product, you might add a topic... (112 words)
- [What is the community? – When](/content/support/hc/en-us/community/posts/26105228086547/index.html): The Help Center community consists of posts and comments organized by topic. Posts might include tips, feature requests, or questions.... (150 words)
- [General Discussion – When](/content/support/hc/en-us/community/topics/26105179529235-general-discussion/index.html) (49 words)
- [I'd like a way for users to submit feature requests – When](/content/support/hc/en-us/community/posts/26105228159891/index.html): You can add a topic like this one in your community. End users can add feature requests and describe their use cases. Other users can... (53 words)
- [How does Jamie work? – When](/content/support/hc/en-us/articles/28326496708755-how-does-jamie-work/index.html): Using a chat-like experience, it walks a person through a series of questions to determine the most suitable options, and it integrates... (67 words)
- [How do I get around the community? – When](/content/support/hc/en-us/community/posts/26105179556755/index.html): You can use search to find answers. You can also browse topics and posts using views and filters. See Getting around the community. (33 words)
- [Eligible uses of When Benefit funds – When](/content/support/hc/en-us/articles/28327826142227-eligible-uses-of-when-benefit-funds/index.html): Employees may be reimbursed from their When Benefit for health insurance premiums that occur after their job loss. In order for a request... (149 words)
- [When Benefit – When](/content/support/hc/en-us/sections/28327000799763-when-benefit/index.html) (29 words)
- [Feature a post – When](/content/support/hc/en-us/community/posts/26105228119443/index.html): Community Managers and moderators can get traction for certain posts by featuring them in a topic in your Help Center community. Learn more (33 words)
- [User profile for Jeremy Leon – When](/content/support/hc/en-us/profiles/26105225749267-jeremy-leon/index.html): Recent activity and contributions by Jeremy Leon (35 words)
- [What is Jamie? – When](/content/support/hc/en-us/articles/28312990448019-what-is-jamie/index.html): Jamie, Health Insurance Advocate, is an innovative tool designed specifically to assist employees who have been laid off or are exiting a... (64 words)
- [Why would someone want to use Jamie? – When](/content/support/hc/en-us/articles/28326433585939-why-would-someone-want-to-use-jamie/index.html): With Jamie, recently laid off employees can easily find and compare health insurance options that best suit their needs and budget.... (53 words)
- [Why use Jamie instead of COBRA? – When](/content/support/hc/en-us/articles/28326485691923-why-use-jamie-instead-of-cobra/index.html): Jamie is a great resource for people who are looking for more affordable options than COBRA. It allows someone to compare plans and... (56 words)
- [What happens if I lost my job and it isn't during an open enrollment period? – When](/content/support/hc/en-us/articles/28326370874003-what-happens-if-i-lost-my-job-and-it-isn-t-during-an-open-enrollment-period.html): If you lose your job and your job-based health insurance coverage as a result, you may be eligible for a special enrollment period to... (194 words)
- [Feature Requests – When](/content/support/hc/en-us/community/topics/26105228140691-feature-requests/index.html) (26 words)
- [I'd like a way for users to submit feature requests – When](/content/support/hc/en-us/community/posts/26105228159891-i-d-like-a-way-for-users-to-submit-feature-requests.html): You can add a topic like this one in your community. End users can add feature requests and describe their use cases. Other users can... (51 words)
- [How do I get around the community? – When](/content/support/hc/en-us/community/posts/26105179556755-how-do-i-get-around-the-community/index.html): You can use search to find answers. You can also browse topics and posts using views and filters. See Getting around the community. (33 words)
- [What is the When Benefit? – When](/content/support/hc/en-us/articles/26105179510419-what-is-the-when-benefit/index.html): The When Benefit is a valuable financial benefit for employees to help make post-employment health insurance more affordable and... (370 words)
- [What is When – When](/content/support/hc/en-us/sections/26105228019219-what-is-when/index.html) (35 words)
- [Navigating Coverage Gaps and ACA Enrollments – When](/content/support/hc/en-us/articles/49632374504083-navigating-coverage-gaps-and-aca-enrollments.html): Navigating a Coverage Gap When Switching to an Individual Health PlanOverviewWhen you lose employer-sponsored health coverage, you have... (1,353 words)
- [Why would I use Jamie instead of Healthcare.gov? – When](/content/support/hc/en-us/articles/28326611580179-why-would-i-use-jamie-instead-of-healthcare-gov.html): The Health Insurance Marketplace, which is accessible through Healthcare.gov, is a government-run platform that allows individuals to... (129 words)
- [What is the ACA MarketPlace or Exchange? – When](/content/support/hc/en-us/articles/28325779128467-what-is-the-aca-marketplace-or-exchange.html): The ACA Marketplace, also known as the health insurance marketplace, is an online platform where individuals and small businesses can... (102 words)
- [Posts – When](/content/support/hc/en-us/community/posts/index.html) (94 words)
- [User profile for Carly Keller – When](/content/support/hc/en-us/profiles/27982206306707-carly-keller/index.html): Recent activity and contributions by Carly Keller (339 words)
- [Search results – When](/content/support/hc/en-us/search/index.html) (72 words)
- [What is an open enrollment period for health insurance? – When](/content/support/hc/en-us/articles/28326316088595-what-is-an-open-enrollment-period-for-health-insurance.html): An open enrollment period for health insurance is a specific period of time each year during which individuals can enroll or make changes... (223 words)
- [General – When](/content/support/hc/en-us/categories/26105227966099-general/index.html) (197 words)
- [Submit a request – When](/content/support/hc/requests/new/index.html) (65 words)
- [What is an Individual Coverage Health Reimbursement Account (ICHRA)? – When](/content/support/hc/en-us/articles/46854788918931-what-is-an-individual-coverage-health-reimbursement-account-ichra.html): An Individual Coverage HRA (ICHRA) is a benefit your employer provides to help pay for your individual health insurance. Instead of... (231 words)
- [Topics – When](/content/support/hc/en-us/community/topics/index.html) (102 words)
- [What is a Special Enrollment Period – When](/content/support/hc/en-us/articles/28328981788947-what-is-a-special-enrollment-period/index.html): Outside of open enrollment, you can only enroll in or change Marketplace plans if you qualify for a Special Enrollment Period based on... (145 words)
- [Online application error – When](/content/support/hc/en-us/articles/28368753373459-online-application-error/index.html): If you are having issues applying through the "enroll now" button, please be advised that the below actions could prevent the... (47 words)
- [How do I check my When Benefit amount? – When](/content/support/hc/en-us/articles/28368716542867-how-do-i-check-my-when-benefit-amount.html): To access your When Benefit amount and submit reimbursements, please login to your custom employee portal through the link provided in... (34 words)
- [Troubleshooting – When](/content/support/hc/en-us/sections/28368618818963-troubleshooting/index.html) (15 words)
- [ICHRA Frequently Asked Questions – When](/content/support/hc/en-us/sections/46854755095443-ichra-frequently-asked-questions/index.html): Get all your questions about your ICHRA benefit answered here. If you still need help, contact support@forwhen.com. (13 words)
- [Individual Coverage Health Reimbursement Account (ICHRA) – When](/content/support/hc/en-us/categories/46854513001875-individual-coverage-health-reimbursement-account-ichra.html) (13 words)
- [Trust Center - When](/content/trust/controls/index.html): Trust Centers are the fastest and most transparent way to demonstrate your company's commitment to security (622 words)
- [Trust Center - When](/content/trust/resources/index.html): Trust Centers are the fastest and most transparent way to demonstrate your company's commitment to security (34 words)
- [2024 Year in Review: A Year of Better Healthcare Choices](/content/explore/blog/2024-year-in-review-a-year-of-better-healthcare-choices.html): When's 2024 year in review: a year of growth and better healthcare choices for the thousands of companies and people we supported through change. (517 words)
- [COBRA Is Your Most Underleveraged Service Line — How Benefits TPAs Can Change That](/content/explore/blog/cobra-is-your-most-underleveraged-service-line-e2-80-94-how-benefits-tpas-can-change-that.html): For most benefits TPAs, COBRA is a thin-margin checkbox. How to turn your most underleveraged service line into real revenue and differentiation. (1,205 words)
- [How COBRA Is Quietly Driving Up Healthcare Costs for Self-Insured Employers](/content/explore/blog/how-cobra-is-quietly-driving-up-healthcare-costs-for-self-insured-employers.html): For self-insured employers, COBRA claims come straight from your pocket. How COBRA quietly drives up costs, and what actually reduces exposure. (1,387 words)
- [Why Proactive Medicare Support Delivers ROI](/content/explore/blog/why-proactive-medicare-support-delivers-roi/index.html): Medicare questions land on HR desks by default. Why proactive, licensed Medicare support cuts offboarding costs and delivers measurable ROI. (786 words)
- [COBRA’s Mid-Life Crisis Hits at 39](/content/explore/blog/cobras-mid-life-crisis-hits/index.html): At 39, COBRA faces challenges its 1986 creators never imagined: mass layoffs and soaring healthcare costs. Why the bridge is buckling now. (1,073 words)
- [What HR Can and Can’t Say About Medicare (Without a License)](/content/explore/blog/what-hr-can-and-cant-say-about-medicare/index.html): HR teams help employees with Medicare every day, often crossing a compliance line they can't see. What you can and can't say without a license. (1,393 words)
- [The Captive Blind Spot at the Exit Door](/content/explore/blog/captive-insurance-blind-spot-at-exits/index.html): Captives manage risk brilliantly for active members, then lose the thread at the exit. The COBRA blind spot quietly costing captive owners money. (1,013 words)
- [The True Cost of Offboarding: A Look Beyond the Last Paycheck](/content/explore/blog/breaking-down-information-silos-with-the-right-digital-toolkit.html): The true cost of offboarding goes well beyond the last paycheck. What poor exits and 'revenge quitting' really cost employers, and how to fix it. (775 words)
- [The Future of Healthcare: Finding Your Place in the Medical Revolution](/content/explore/blog/the-future-of-healthcare-finding-your-place-in-the-medical-revolution-2.html): AI that predicts illness, virtual visits, and DNA-tailored treatment: finding your place in a healthcare revolution that's already reshaping care. (745 words)
- [Buyouts vs Layoffs: A Complete Guide to Workforce Reduction Options](/content/explore/blog/buyouts-vs-layoffs-a-complete-guide-to-workforce-reduction-options.html): Buyouts vs layoffs: a complete guide to workforce-reduction options in 2025, and how to support employees through either kind of transition. (598 words)
- [The Rise of Revenge Quitting: Why Employees Are Taking a Stand in 2025](/content/explore/blog/revenge-quitting-workplace-trends-2025/index.html): Revenge quitting is rising in 2025. The workplace trends driving employees to take a stand, and what it signals for employers and offboarding. (748 words)
- [AI in Employee Benefits: From Chatbot Curiosity to the Most Important Decision Your Departing Employees Will Ever Make](/content/explore/blog/ai-in-employee-benefits/index.html): AI in employee benefits is more than a chatbot. How it's reshaping the most important decision departing employees make: choosing health coverage. (1,086 words)
- ["Our Plan Is Too Rich. They'll Always Choose COBRA."](/content/explore/blog/health-insurance-plan-is-too-rich/index.html): 'Our plan is too rich, they'll always choose COBRA.' The data disagrees: 80-90% of eligible employees pick something else. Why the assumption fails. (989 words)
- [How Self-Funded TPAs Can Help Clients Reduce COBRA Claims Exposure](/content/explore/blog/how-self-funded-tpas-can-help-clients-reduce-cobra-claims-exposure.html): COBRA participants are higher utilizers thanks to adverse selection. How self-funded TPAs can finally help clients reduce COBRA claims exposure. (1,048 words)
- [How to Update Your Severance Policy Without the Drama: A Practical Guide](/content/explore/blog/practical-guide-to-changing-severance-policy/index.html): A practical guide to modernizing your severance policy: map the messy current state, align COBRA subsidies, and update language without the drama. (751 words)
- [Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.](/content/explore/blog/levers-brokers-can-pull-during-renewals/index.html): 2027 renewals are landing worse than the averages suggest. The two levers benefits consultants can actually pull to move the number for clients. (1,203 words)
- [The Hidden Costs of Poor Employee Offboarding](/content/explore/blog/the-hidden-costs-of-poor-employee-offboarding/index.html): The final chapter of the employee lifecycle rarely gets its due. The hidden costs of poor offboarding, from a CEO who has lived the layoff too. (679 words)
- [Your COBRA Subsidy Is Costing You Double. Here's the Fix.](/content/explore/blog/cobra-subsidy-vs-when-benefit/index.html): COBRA subsidies feel generous but can cost employers twice. The financial trap in subsidizing COBRA, and a fix that helps your people and budget. (1,019 words)
- [COBRA Administrators: From Compliance Vendor to Strategic Partner](/content/explore/blog/cobra-administrators-from-compliance-vendor-to-strategic-partner.html): COBRA administration is being commoditized. How administrators move from compliance vendor to strategic partner and defend their revenue. (1,032 words)
- [A When Story - Meet Nicole](/content/explore/blog/a-when-story-nicole/index.html): A When story: Nicole, a primary earner and finance leader, shares how she navigated health coverage through a major career transition with When. (658 words)
- [The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.](/content/explore/blog/salary-everyone-sees-insurance-no-one-talks-about/index.html): Everyone talks salary; nobody talks the health insurance gap that follows a job change. What income data misses about coverage during transitions. (853 words)
- [COBRA Is a Known Underwriting Problem. When Is the Solution Carriers Haven't Had.](/content/explore/blog/cobra-is-a-known-underwriting-problem/index.html): Carriers have priced around COBRA adverse selection for years. When is the solution underwriters never had, and how it changes the risk-pool math. (1,056 words)
- [How PEOs Are Turning Offboarding into a Competitive Edge](/content/explore/blog/how-peos-are-turning-offboarding-into-a-competitive-edge.html): A 58-year-old on your master plan for 18 months is a hidden cost. How PEOs turn offboarding from a compliance task into a competitive edge. (900 words)
- [The Story of When: Two neighbors' mission to fill America's Healthcare Gap.](/content/explore/blog/when-founders-story/index.html): How a $2,100 insurance bill after a layoff sparked When: two neighbors' mission to fill America's healthcare gap for people between jobs. (484 words)
- [Why Our Agents Don't Work on Commission](/content/explore/blog/why-our-agents-dont-work-on-commission/index.html): Most health insurance agents earn more when you choose certain plans. Why When's agents don't work on commission, and how that protects you. (839 words)
- [Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.](/content/explore/blog/delaying-retirement-to-afford-health-insurance/index.html): A third of Americans cut basic expenses to afford care, and many delay retirement for coverage. Why employers can't look away from the tradeoffs. (681 words)
- [When Status - Incident History](/content/status/history/index.html): When's Incident and Scheduled Maintenance History (27 words)
- [status/history-rss.html](/content/status/history-rss.html) (83 words)
- [status/history-atom.html](/content/status/history-atom.html) (84 words)
- [What is Health Insurance?](/content/explore/blog/what-is-health-insurance/index.html): Health insurance basics: how premiums, deductibles, and coverage work to protect you and your family from the high cost of medical care. (748 words)
- [What is COBRA?](/content/explore/blog/what-is-cobra/index.html): What is COBRA? A plain-English guide to the federal law that lets you continue employer health coverage after a job loss, and what it really costs. (756 words)
- [Client Saved $1.4M in 3 Months with When’s Workforce Transitions Platform](/content/explore/blog/chicago-tech-consulting/index.html): How one company turned workforce transitions into $1.4M in savings in three months with When, while giving departing employees better support. (655 words)
- [The Birth of When](/content/explore/blog/the-birth-of-when/index.html): The Birth of When: how a 2008 business-school idea about COBRA and job loss grew into a platform for supporting people through career transitions. (372 words)
- [Picking Insurance Plans with When](/content/explore/blog/picking-insurance-plans-with-when/index.html): How to pick an insurance plan with confidence: what to weigh on coverage, cost, networks, and prescriptions, and how When guides the choice. (580 words)
- [Terms of Service | When](/content/pages/terms-of-service/index.html): When's terms of service: the terms governing use of When's website and AI-powered workforce transitions platform for employers and their employees. (4,876 words)
- [Privacy Policy | When](/content/pages/privacy-policy/index.html): Read When's privacy policy: how we collect, use, and protect the personal information of the people and employers who use our workforce transitions platform. (2,720 words)
- [When Status - Uptime History](/content/status/uptime/index.html): When's Uptime History (9 words)
- [When Blog: COBRA, Medicare & Workforce Transitions](/content/explore/blog/index.html): The When blog: practical insight on COBRA alternatives, workforce transitions, Medicare, and turning layoffs into savings for employers and their people. (530 words)
- [COBRA Qualifying Events: The Full List Beyond Layoffs](/content/explore/blog/cobra-qualifying-events/index.html): COBRA has seven qualifying events, not one. Employers plan for layoffs and miss the other six, several of which run 36 months and skew high-cost. (1,451 words)
- [Your Aging Workforce Is a Benefits Cliff. Here's the Data.](/content/explore/blog/aging-workforce-medicare-benefits-cliff/index.html): At 65, your employees hit a benefits cliff most HR teams never see in the data. What an aging workforce really costs, and how to get ahead of it. (1,109 words)
- [The Best Cost-Containment Solution Is the One You Can Implement the Fastest](/content/explore/blog/easiest-cost-containment-solution-to-implement/index.html): The fastest cost-containment win hides in plain sight: COBRA claims. Why the health plan report misses it, and how employers can act on it now. (1,106 words)
- [Advisory Firm vs. Licensed Agency: Who Can Actually Enroll?](/content/explore/blog/advisory-vs-licensed-agency/index.html): Advisory firms can recommend a plan but can't enroll anyone. See why When's licensed agency model gets departing employees actually covered. (1,077 words)
- [It's Not If, It's When: Build Your Off-Boarding Plan Before You Need It](/content/explore/blog/build-offboarding-plan-before-the-rif/index.html): Layoffs rarely arrive without warning. The smartest time to set up a workforce-transition solution like When is before the announcement, not after. (916 words)
- [When Solutions: COBRA Alternatives for Every Exit](/content/solutions/index.html): When's solutions cover every workforce transition, from layoffs and retirement to Medicare, turning COBRA liability into measurable savings. (624 words)
- [Tom Cox - When - The AI Workforce Transitions Platform](/content/explore/about/tom-cox/index.html): Tom Cox is Channel Sales Manager at When, where he focuses on building strategic partnerships with TPAs, Health Plans, and COBRA administrators to modernize workforce transitions through AI-powered solutions. With over 20 years of experience in benefits administration technology, Tom has built a career architecting and scaling channel sales programs that drive revenue and accelerate market penetration. His background includes leadership roles at WEX Health, Alegeus, and other healthcare technology companies. Tom specializes in translating complex technology into clear business value and is passionate about how AI is transforming HR functions, benefits technology, and the employee benefits experience. (240 words)
- [Carly Keller - When - The AI Workforce Transitions Platform](/content/explore/about/carly-keller/index.html): Naval Academy graduate and former Navy officer who led Operations at ApartmentJet through its Expedia acquisition, where she then built and managed large client service teams at Expedia. (170 words)
- [PEPM Is Predictable. Utilization Is Aligned. Why We Offer Both.](/content/explore/blog/pepm-vs-utilization-pricing-why-offer-both/index.html): PEPM gives you one predictable number. Utilization-based pricing tracks actual cost. How to choose, who carries the risk, and why When offers both. (857 words)
- [When Partners with Iowa State University, Helping Graduates Navigate Health Insurance | When](/content/explore/press-news/when-partners-with-iowa-state-university/index.html): When partners with Iowa State University to help graduating students navigate health insurance as they leave the campus health plan. (687 words)
- [When CEO Andy Hamilton Featured in "All the Cool Girls Get Fired" | When](/content/explore/press-news/when-ceo-featured-in-all-the-cool-girls-get-fired/index.html): When CEO Andy Hamilton is featured in 'All the Cool Girls Get Fired,' on facing health insurance and identity after being let go. (797 words)
- [P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients | When](/content/explore/press-news/p-a-group-partners-with-when/index.html): P&A Group partners with When to deliver healthcare transition support to employer clients, cutting COBRA costs and improving the exit experience. (688 words)
- [When Raises $10M Series A: Building the Bridge Across America's Healthcare Gap | When](/content/explore/press-news/when-raises-10m-series-a/index.html): When raises a $10.2M Series A to bridge America's healthcare gap, following 4.3x YoY revenue growth and 6,200+ companies on the platform. (752 words)
- [When Welcomes Tara Conger to Board of Directors | When](/content/explore/press-news/tara-conger-joins-board-of-directors/index.html): When welcomes HR strategy leader Tara Conger to its Board of Directors as it scales support for employees through career transitions. (492 words)
- [When Platform: AI Health Insurance Guidance & Concierge](/content/platform/index.html): When's AI platform gives departing and Medicare-eligible employees personalized coverage options with licensed, commission-free guidance. (632 words)
- [Brook West Joins When as Chief Revenue Officer | When](/content/explore/press-news/brook-west-named-cro-press-coverage/index.html): When welcomes Brook West as its first Chief Revenue Officer. See what Crain's Chicago Business, HR Tech Cube, GeekWire, and others are saying about the appointment. (402 words)
- [When: The AI-Powered Platform for COBRA Alternatives, Medicare Transitions & Layoff Support](/content/404/index.html): 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 RIFs. (18 words)
- [Andy Hamilton - When - The AI Workforce Transitions Platform](/content/explore/about/andy-hamilton/index.html): Serial entrepreneur and multifamily tech veteran who co-founded and led ApartmentJet through its successful acquisition by Expedia Group, where he subsequently ran operations for their multifamily division. (207 words)
- [Press & News | When](/content/explore/press-news/index.html): Official press releases and media coverage from the When newsroom. (181 words)
- [COBRA Savings Calculator for Employers | When](/content/explore/savings-calculator/index.html): See how much your company could save by offering employees a better alternative to COBRA. Calculate your potential savings in under a minute. (335 words)
- [When Named Most Innovative at isolved Connect for Partners 2026 | When](/content/explore/press-news/when-named-most-innovative-isolved-connect-2026/index.html): When is named Most Innovative at isolved Connect for Partners 2026, recognized for changing the workforce transitions market with real results. (425 words)
- [Brook West - When - The AI Workforce Transitions Platform](/content/explore/about/chief-revenue-officer/index.html): Veteran SaaS commercial leader with two decades scaling healthcare and technology revenue organizations, holding senior leadership roles at Carrum Health, 98point6, Valant, and Fuze while building teams from early stage to category leadership. (145 words)
- [Jeremy Leon - When - The AI Workforce Transitions Platform](/content/explore/about/jeremy-leon/index.html): Former actuary and HR/Benefits expert at Tesla and Mercer who designed benefit plans and managed costs for enterprise clients and thousands of employees. (137 words)
- [In Fast Company: Why Leaders Shouldn’t Blame Layoffs on AI | When](/content/explore/press-news/andy-hamilton-fast-company-ai-layoffs/index.html): CEO Andy Hamilton writes for Fast Company on why leaders should think twice before blaming layoffs on AI, and why the story you tell the market has to match the one you tell your people. (335 words)
- [Patrick Koeller - When - The AI Workforce Transitions Platform](/content/explore/about/patrick-koeller/index.html): Technical co-founder and proven engineering leader with a track record of scaling startups to successful exits, including building Print Syndicate to $40M in annual revenue and orchestrating ApartmentJet's acquisition by Expedia Group.  (156 words)
- [In HR Tech Cube: The Medicare Transition Employers Can’t Ignore | When](/content/explore/press-news/dan-wertheimer-hrtechcube-medicare/index.html): Co-Founder Dan Wertheimer writes for HR Tech Cube on the aging workforce, the compliance rules that tie employers’ hands, and why proactive Medicare support belongs in every benefits strategy. (264 words)
- [Dan Wertheimer - When - The AI Workforce Transitions Platform](/content/explore/about/dan-wertheimer/index.html): Fortune 50 innovation executive who led Target's digital transformation as Senior Director of Innovation, building their marketplace strategy and managing their global accelerator portfolio including Target + Techstars and Target Takeoff.  (193 words)
- [On the Podcast: Andy Hamilton Talks COBRA, AI, and Building When | When](/content/explore/press-news/andy-hamilton-lifes-a-pitch-podcast/index.html): CEO Andy Hamilton joins the Life’s a Pitch podcast to talk about broken COBRA experiences, building When, and where AI actually helps in healthcare navigation. (217 words)
- [When Medicare: Proactive Transition Support for Employers](/content/medicare/index.html): When helps employers guide Medicare-eligible employees off group plans with personalized support that lowers high-cost claims and eases every transition. (542 words)
- [When: The AI-Powered Platform for COBRA Alternatives, Medicare Transitions & Layoff Support](/content/customers/index.html): 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 RIFs. (54 words)

## About Pages

- [Contact When: Schedule a Demo or Get in Touch](/content/explore/contact/index.html): Have questions about When's workforce transitions platform? Reach out to our team to schedule a demo, request a quote, or learn how When can reduce your COBRA costs. (846 words)
- [About When: The Team Behind the Platform](/content/explore/about/index.html): Meet the team behind When: insurance experts, technologists, and advocates building the AI platform for employee healthcare transitions. (341 words)

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