Kept is a modern COBRA administration platform that uses automated compliance as the wedge to build a long-term B2C relationship with departing employees — cross-selling Medicare/Medicaid guidance, insurance placement, financial help, and job placement, with revenue share on each placement. The bet is that COBRA is one of the last B2B-billed touchpoints in an employee's benefits journey that hasn't been consumer-productized.
Team is HMC-quality: Haak Saxberg (co-founder, HMC, technical lead) and Topher Reynoso (co-founder, University of Washington, ex-PlanGrade — Autodesk sub). Company is based in LA and has raised $2.1M to date (Web). Raising a $2.5M seed with SH getting an inside look. Two calls on July 3 signal both team eagerness and SH's active interest.
COBRA administration is a $1.4B TPA market where 75%+ of employers already use a third party (Web). The wedge is not the compliance market itself — it's the consumer-side wallet share that opens when a compliance TPA sits in the flow. Every departing employee is at a healthcare, financial, and career-decision inflection: the platform that owns the compliance moment has the shortest path to those cross-sells.
| Player | Positioning | Funding / Stage | Edge vs. them |
|---|---|---|---|
| Kept | Automated COBRA + B2C service layer for departing employees | Seed | — |
| Ameriflex | Enterprise COBRA TPA | Private, established | Ameriflex is B2B pure; Kept adds consumer relationship + monetization |
| Navia Benefits | Established COBRA + benefits TPA | Private | Same — legacy admin, no consumer motion |
| WEX / HealthEquity | Benefits admin platforms | Public | Larger platforms; not focused on the COBRA-lives cross-sell |
| Rippling / Justworks | Modern HR / benefits with COBRA add-on | Late-stage private | HR platforms could integrate COBRA + off-boarding but haven't yet |
Moat: The moat is the consumer relationship — legacy TPAs (Ameriflex, Navia) have compliance workflow but no reason to keep talking to the employee after the COBRA election. Kept's monetization on downstream placements is a category-native business model that legacy players would have to rebuild consumer trust to enter.
Strategic acquirers: WEX ($6B benefits-admin roll-up), HealthEquity (public), Rippling, Justworks, ADP, and the private-equity roll-up market that has consolidated COBRA TPAs over the past decade. Consumer-insurance-platform buyers (SelectQuote, GoHealth) could also acquire for the placement revenue. At a seed cap likely in the $10–15M range, 10–20x is plausible on strategic outcome.
First substantive call — Kept raising $2.5M seed. Discussed automation-as-wedge and consumer cross-sell business model.
Second call same day for a deeper technical + team walkthrough.