When is an AI-driven platform designed to streamline the post-employment experience. By connecting existing employees with more affordable health insurance options and added services like career counseling and resume building, When provides support for employees navigating offboarding, all while saving your company time and money. Pulse 2.0 interviewed When co-founder and CEO Andy Hamilton to learn more about the company.
Andy Hamilton’s Background
What is Andy Hamilton’s background? Hamilton said:
“I am a serial entrepreneur, having previously co-founded two technology startups that were later acquired by public companies. The latter company, ApartmentJet was acquired by Expedia Group. During the Covid pandemic, I experienced a layoff firsthand and it motivated me to create a better offboarding solution. In my downtime I enjoy playing tennis, working out on my Peloton and reading.”
Formation Of The Company
How did the idea for the company come together? Hamilton shared:
“The idea for When was conceived by my co-founder and next-door neighbor, Dan Wertheimer, after he lost his job while pursuing his MBA at Chicago Booth. His health insurance premiums jumped from $50 to $800 a month, and this experience led Dan to develop a business thesis on creating a new employee benefit to help cover health insurance costs during job loss. Dan submitted the thesis to the New Venture Challenge, one of the largest business case competitions in the world, run by the University of Chicago. While the idea received great feedback, Dan didn’t have a team in place to bring it to life. Fast forward 10 years, when I was laid off from Expedia Group, and for the first time, I understood the pain of being laid off. That’s when we decided to bring the idea to life.”
Favorite Memory
What has been your favorite memory working for the company so far? Hamilton reflected:
“Supporting our first member/employee with a When Benefit that allowed her to find a more affordable health insurance plan. By downsizing her plan, she was able to stretch her When Benefit from covering three months to eight months of health insurance. This experience became a pivotal moment for us, validating our hypothesis: individuals navigating a job transition value the flexibility to choose their own plan and often opt for more economical options to extend their coverage duration.”
Core Products
What are the company’s core products and features? Hamilton explained:
“When is a post-employment solution that uses an AI assistant to help exiting employees maintain access to healthcare by providing affordable alternatives to COBRA. We offer personalized solutions that allow employees to compare their COBRA plan side by side with ACA and off-exchange plans available on the public market, as well as a white-glove support team to assist employees during this critical transition period. When is a win – win for the employer and employee, saving a tremendous amount of time and money on both sides. Employers have the opportunity to save money by reducing exposure to high-cost COBRA claims, and employees can save a lot of money by finding alternatives to COBRA with equivalent, or potentially even better, coverage. When provides more than just health insurance, we also offer support in various career transitions including partnerships with job search firms and career development services.”
Challenges Faced
What challenges has Hamilton and the team faced in building the company? Hamilton acknowledged:
“The biggest challenge we’ve faced is helping companies understand that COBRA isn’t just an administrative choice – it’s a strategic decision that impacts both their bottom line and their people. Many organizations default to COBRA out of habit, not realizing it typically costs them 3x more than active employees through high-cost claims. We’ve overcome this by focusing on data and real results. When our partners see that transitioning employees away from COBRA towards better alternatives can reduce their exposure by up to 70% while providing better support to their former colleagues, the conversation shifts from ‘Why change?’ to ‘How soon can we start?’”
“Another challenge has been the rapid evolution of the workforce landscape. With over 700,000 Americans facing job transitions last year – the highest since the early 2000s – the need for better transition support has never been more critical. We’ve adapted by enhancing our AI capabilities and expanding our support services to handle increased volume while maintaining personalized guidance for each individual.”
Evolution Of The Company’s Technology
How has the company’s technology evolved since launching? Hamilton noted:
“This year, we introduced a major upgrade to our AI-powered health insurance marketplace. The platform equips employees with the tools to compare existing coverage with a range of options, including plans from Healthcare.gov, state exchanges like Covered California, and private providers. Our AI assistant Jamie analyzes each individual’s unique needs to deliver tailored recommendations, helping people make informed decisions about their post-employment coverage.”
Significant Milestones
What have been some of the company’s most significant milestones? Hamilton cited:
“In the last year we’ve hit many milestones, including bringing our service for the first time to graduating students through a partnership with Iowa State University.. Last August, we raised $4.6 million in a seed funding round led by B Capital, and in October, we were named one of Business Insider’s Most Promising Fintech Startups. This industry recognition is encouraging as it shows our work is having an impact in changing the status quo of how employers treat employees as they leave a company.”
Customer Success Stories
When asking Hamilton about customer success stories, he highlighted:
“On average, companies using our When Benefit have seen an 80% shift from COBRA to alternative plans, reducing healthcare costs by up to 70%. One example, our collaboration with West Monroe Partners led to a 83% reduction in COBRA enrollments, saving the company $1.4 million in medical claims. Similarly, our partnership with iSolved HCM, which now brings our service to over 7 million employees, saw over 80% adoption rate in its first month, signaling strong demand for our solutions.”
Funding/Revenue
When asking Hamilton about the company’s funding and revenue details, he revealed:
“We have raised $4.6 million in seed funding, and are not disclosing revenue at this time.”
Total Addressable Market
What total addressable market (TAM) size is the company pursuing? Hamilton assessed:
“We’re pursuing the roughly 65M non-farm workers in the U.S. who receive employer-sponsored health insurance and work at companies that are required to offer COBRA (minimum of 20 employees).”
Differentiation From The Competition
What differentiates the company from its competition? Hamilton affirmed:
“When was founded on the belief that the status quo exit experience falls short for both employees and employers. We’re reshaping how businesses handle employee exits by transforming offboarding into a critical brand touchpoint. Our platform goes beyond standard HR procedures, using AI and data-driven insights to streamline health insurance options, provide personalized support to departing employees, and reduce financial exposure for employers.”
“Despite investing heavily in onboarding, companies typically overlook the exit experience and therefore default to expensive COBRA options, creating a significant blind spot in how companies support departing employees. Our AI-powered platform empowers employees to compare COBRA alongside alternatives like ACA plans, helping them find coverage that truly fits their needs. By providing transparent options and personalized guidance, we’re helping companies reduce costs while ensuring departing employees get the support they deserve.”
Future Company Goals
What are some of the company’s future goals? Hamilton emphasized:
“We envision a future where every exiting employee has access to real support, not just a folder of PDFs and a COBRA packet. Where exits aren’t just administrative tasks, but opportunities to demonstrate our values and protect our people. We’re building toward this future by expanding our platform’s capabilities, growing our team, and forging strategic partnerships that help us reach more organizations. Because at the end of the day, this isn’t just about reducing costs or mitigating risks – it’s about making career transitions more human.”
Additional Thoughts
Any other topics you would like to discuss? Hamilton concluded:
“Yes. There are a couple of trends we are noticing that are often overlooked when it comes to the post-employment experience. The first is the disconnect between what HR teams think they provide, and what employees say they experience, with a significant communication gap existing between HR leaders and workers. While 45% of HR leaders claim to offer career coaching and access to outplacement services, only 10% and 9% of workers, respectively, report receiving these services (LHH).”
“The second trend is the impact of layoffs on the remaining workforce. A layoff as small as 1% of your workforce can result in up to 31% more employees leaving your organization within the following year. Transition assistance offered to laid off workers can help restore that confidence, keeping more of your workers on board through a challenging time. (HBR 2018) In a 2002 study, researchers found that after a layoff, survivors experienced a 41% decline in job satisfaction, a 36% decline in organizational commitment, and a 20% decline in job performance. These are trends that are not only concerning from an HR perspective, but from a broader business perspective as well.”
