### Andy Hamilton

### Founder & CEO

**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. Andy brings deep expertise in scaling B2B marketplaces and a mission-driven focus on transforming the employee offboarding experience, having identified the critical gap in post-employment healthcare coverage that When addresses. His unique combination of operational excellence from building enterprise SaaS platforms and firsthand understanding of HR pain points positions him to revolutionize how companies manage employee transitions.

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**The Salary Number Everyone Sees. The Health Insurance Gap Nobody Talks About.**\ 
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Andy Hamilton](/content/explore/blog/salary-everyone-sees-insurance-no-one-talks-about/index.html)

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**Americans Are Rationing Medicine to Afford Health Care. Employers Can't Look Away.**\ 
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Andy Hamilton](/content/explore/blog/delaying-retirement-to-afford-health-insurance/index.html)

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**When Raises $10M Series A: Building the Bridge Across America's Healthcare Gap**\ 
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Andy Hamilton](/content/explore/blog/when-raises-10m-series-a/index.html)

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**How COBRA Is Quietly Driving Up Healthcare Costs for Self-Insured Employers**\ 
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Andy Hamilton](/content/explore/blog/how-cobra-is-quietly-driving-up-healthcare-costs-for-self-insured-employers/index.html)

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**The Hidden Costs of Poor Employee Offboarding**\ 
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Andy Hamilton](/content/explore/blog/the-hidden-costs-of-poor-employee-offboarding/index.html)

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**Buyouts vs Layoffs: A Complete Guide to Workforce Reduction Options**\ 
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Andy Hamilton](/content/explore/blog/buyouts-vs-layoffs-a-complete-guide-to-workforce-reduction-options/index.html)

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**2024 Year in Review: A Year of Better Healthcare Choices**\ 
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Andy Hamilton](/content/explore/blog/2024-year-in-review-a-year-of-better-healthcare-choices/index.html)

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**The Birth of When**\ 
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Andy Hamilton](/content/explore/blog/the-birth-of-when/index.html)