Transforming Post-Acute Care Operations with the Power of AI: Inside Kevin Calcado’s Journey to Build Claim Health

Founder 101
Lisa Shmulyan
September 11th, 2025
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Healthcare is one of the most important services in life. Especially post-acute care, such as home health, hospice, and skilled nursing, that supports people in their times of greatest need. 

But many post-acute care organizations are drowning in complex billing processes, reliant on manual workflows and tedious data entry to cover the care provided. Despite many industries having embraced digital transformation in recent years, the post-acute care space has remained largely unchanged. And with the number of aging people requiring post-acute care increasing every year, these operational inefficiencies are being put to the test, often resulting in lost revenue opportunities and negative patient experiences. 

Kevin Calcado and his co-founder, Jayen Ram, with more than a decade of SaaS experience and backgrounds in healthcare tech, had a front-row seat to the meteoric rise of AI in recent years, and quickly recognized that AI could transform the legacy workflows in post-acute care. So they set out to build Claim Health, aiming to help organizations increase back-office efficiency, protect revenue, and deliver better patient experiences.

Introducing Claim Health: The AI-Powered Billing Platform for Home-Based Care

Claim Health is an automated billing platform that helps home healthcare agencies streamline eligibility, authorizations and claims processing so that they can spend less time on manual, repetitive billing processes and more on driving growth. 

Post-acute healthcare organizations must navigate a complex billing system in order to cover the care they provide. The nurses and clinicians that treat patients at home are usually deployed by agencies, who in turn claim reimbursement from government payers and insurance companies for the medical services provided. But to ensure proper reimbursement, agencies must receive and process appointment notes and documentation from nurses on-site, and manually transcribe that information into different portals and platforms. Too often, these tedious workflows result in administrative bottlenecks, denied claims, and unbilled visits, causing post-acute agencies to lose upwards of 15% of their revenue each year.

Claim Health is helping agencies modernize their workflows by putting key billing tasks on autopilot — from eligibility checks and prior authorizations to claim status management and AR follow-up. By connecting to every system in the claims ecosystem—EMRs, clearinghouses, payer portals, and third-party systems—with 24/7 synchronization, the platform enables agencies to streamline claims management and uncover hidden revenue opportunities. And by presenting live financials, claim status updates, and industry benchmarking data in clear, dynamic dashboards, Claim Health helps providers gain a better understanding of performance.

Kevin’s Journey to Claim Health

Kevin first entered healthcare at Dandy, one of the fastest-growing dental tech startups ever, where he joined as the first GTM hire and helped scale from zero to nine-figures in revenue in under three years. It was also during this time that he met Jayen, a Stanford computer science graduate and former Facebook engineer, who would later become Kevin’s co-founder at Claim. 

As Kevin and Jayen witnessed the rapid advancements in AI, they knew that there’d be an opportunity to use modern technology to help legacy sectors like post-acute care modernize their processes and increase revenue. After teaming up to launch Claim Health just six months ago, the team is already backed by Y Combinator and is beginning to partner with post-acute care organizations across the country.

Kevin’s Advice for Fellow Founders

Claim Health has grown rapidly since launch, and Kevin insists that the secret to their progression has been continuous iteration. By shipping quickly and monitoring users’ responses, the team has been able to develop the platform based on real customer feedback rather than building in isolation. As he describes, “ship quickly and always listen to your customers. They really give the best advice."

In addition to monitoring engagement, Kevin and Jayen have invested a lot of time in understanding their customers’ needs and workflows. They spent weeks working out of customers’ offices, shadowing to understand how their customers’ "bespoke workflows actually apply in their day-to-day lives.” This has helped them build a solution that truly provides value to the operators on the front line.

And the approach is working. Thus far, most of Claim’s GTM has been driven by referrals and word-of-mouth, with providers readily sharing their experiences with counterparts across the industry. 

To learn more about Kevin’s journey, you can follow him on LinkedIn or visit claimhealth.com/

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Lisa Shmulyan
Lisa Shmulyan
Contributing Writer and Editor
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