Why We Invested in When

At 7wire Ventures, we invest in companies that address structurally broken parts of the healthcare system by improving choice, experience, and outcomes for individuals, while also helping stakeholders like employers manage cost, risk, and complexity. Workforce transitions are a critical yet underserved moment in the employee lifecycle, with more than 60 million transitions occurring annually in the U.S. due to voluntary exits, layoffs, and retirement. During these events, employers are often reliant on manual, fragmented offboarding processes, and employees are left to navigate confusing and expensive healthcare decisions, frequently defaulting to costly COBRA coverage. The result is higher healthcare costs for employers, increased compliance and reputational risk, and a poor experience for individuals at an already vulnerable time.

Our investment in When reflects our belief that artificial intelligence can be applied meaningfully to moments in healthcare that have historically been manual, fragmented, and reactive. When uses AI to support employers and employees at the point of workforce transition, applying intelligence and personalization to help individuals navigate complex healthcare decisions while enabling employers to manage cost, compliance, and experience at scale. By bringing data and automation to offboarding, When transforms a traditionally administrative process into a more informed and intentional part of the employee lifecycle.

Fixing One of Healthcare’s Most Neglected Transitions

Historically, offboarding solutions have been built to satisfy regulatory requirements rather than help people make better decisions. Employers have been forced to rely on point solutions that handle notices and billing, while departing employees are given little more than static information and limited support at a moment of significant uncertainty. This disconnect leaves employers with limited visibility into outcomes, and employees without the guidance needed to evaluate alternatives, creating a system that is compliant by design but ineffective in practice.

When was created to bridge this gap. Instead of relying on reactive, notice-based workflows, the platform integrates into employer systems to identify transition events and deliver timely, structured support to individuals weighing their next steps. This approach provides employers with meaningful insight into engagement and outcomes, while giving employees a clearer, more navigable path through a process that has historically lacked coordination, context, and accountability.

In practice, employers that have deployed When are seeing meaningful financial and experiential impact. One customer realized $1.4 million in savings in just three months by moving 83% of departing employees away from COBRA to more cost-effective coverage options. Across deployments, individuals have saved an average of $266 per month in premiums, and satisfaction scores have reached 93%. Another employer saw $24,000 in COBRA cost savings per impacted employee. These results demonstrate that better guidance at the point of transition delivers measurable ROI for employers, tangible cost savings for individuals, and a dramatically improved offboarding experience compared to traditional, compliance-only approaches.

Built by Founders Who Know the Problem Firsthand

We were also drawn to the founding team’s combination of deep operational experience and personal conviction. CEO Andy Hamilton and CSO Dan Wertheimer were motivated to start When after navigating their own frustrating offboarding and healthcare transition experiences, giving them firsthand insight into the gaps facing both employers and employees. The team brings significant enterprise and technology leadership experience, with prior roles at companies such as Expedia, Target, and Discover, and a track record of building and scaling SaaS businesses. Complemented by a strong technical foundation led by CTO Patrick Koeller, the founders have demonstrated the ability to translate a clear problem understanding into a thoughtfully built product that is already delivering real-world impact.

“We started When because we experienced firsthand how confusing and stressful healthcare decisions can be during a career transition. Employers want to do the right thing, but the tools haven’t existed to support people in a thoughtful, scalable way. Our goal with When is to bring clarity and intelligence to this moment, helping individuals make better decisions while giving employers a solution that actually works.” – Andy Hamilton, When CEO

Since launching, When has demonstrated strong early traction across a growing base of employers, brokers, and platform partners. The company has achieved 8x year-over-year revenue growth, with momentum driven by a diversified go-to-market approach that includes direct enterprise relationships, broker-led distribution, and embedded platform partnerships. Adoption and engagement have been consistently strong across customer segments, reinforcing the platform’s value proposition and supporting a growing pipeline of larger employers.

The Path Forward

We are excited to partner with the When team and a thoughtful group of investors – ManchesterStory and Enfield Capital Partners – as the company enters its next phase of growth. We believe When is uniquely positioned to help redefine how organizations approach workforce transitions, bringing greater consistency and operational strength to an area that has long lacked both. As adoption grows and the platform continues to evolve, we see the potential for When to become an enduring company in a category that is only beginning to take shape.

More broadly, workforce transitions are emerging as a meaningful inflection point in the healthcare system, influencing cost, access, and experience for millions each year. Improving how this moment is managed presents an opportunity not only to support departing employees, but also to reshape how healthcare decisions are guided during periods of change. We are proud to support When as it advances this mission and works to create a more modern, empathetic, and effective transition experience for employers and individuals alike.