The $254B Check Problem: Insurance Payments go Digital

IntroductionWhy does an industry that talks about digital transformation still pay so many claims by paper check? The answer is not stubbornness; it is complexity, and it is worth billions. Josh Hollander sits down with Kevin Ostrander, Chief Revenue Officer at One Inc, to unpack what it actually takes to move carriers off checks, why multi-party claims payouts are the hard part nobody solved first, and what happens when enough carriers and payees are connected that the network, not the processing, is what carriers are buying.Guest BioKevin Ostrander is Chief Revenue Officer at One Inc, the insurance-specific payments network processing over $245 billion in annual payment volume for more than 300 carriers. He has spent nearly sixteen years selling enterprise technology into insurance, including six years at Thunderhead before its acquisition by Accel-KKR, and he joined One Inc ten years ago when the company had single-digit customers. He owns everything from new business acquisition through customer success.Key Topics-Why checks persist - More than half of claims payouts go to third-party vendors, lienholders, and mortgagees, and fifty states each add their own compliance rules, so single-party digital solutions never covered enough of the workflow.-The malleable ROI case - Checks cost $6 to $25 each fully loaded, digital claim payouts land in minutes instead of days, and the same platform argument works whether the carrier's priority that year is cost, retention, or customer experience.-Adjuster adoption decides outcomes - If issuing a digital payment adds manual steps, adjusters revert to checks, so One Inc pairs its technology with change management, FAQs, and training on the carrier side.-One platform for pay-in and pay-out - Over 40% of One Inc's carriers now run both PremiumPay and ClaimsPay, giving policyholders one wallet across premium payments, refunds, and claims.-The network is the moat - One Inc's escrow network covers 80%+ of escrowed homeowner premium and connects it to 300+ carriers, moving premium 11 to 12 days faster than the 12-to-15-day lockbox process.-Disciplined expansion - Life insurance (AAA Life, Transamerica) and Canada (with Guidewire, which holds 80%+ of Canadian claims administration) came only after the P&C base was solid.-Career advice from a first-time CRO - Kevin's path from single-digit customers to 300+ came down to experience you cannot skip, mentors, and recognizing product-market fit when you have it.Notable Quotes"Fi