Dallas-based 5IR Funds just led a $6.5 million Series A round into HOOTL, an AI automation platform attacking healthcare's most expensive bottleneck: insurance claim processing.
The Charlottesville startup is building specialized AI agents that could finally fix a system bleeding $450 billion annually in denied claims and administrative chaos.
The $450 Billion Problem HOOTL Is Solving

Every year, 850 million insurance claims get rejected in the U.S. healthcare system. Over 90% of medical practices say insurance complexity is their biggest growth barrier.
Providers lose revenue, patients face delays, and administrative teams drown in paperwork. HOOTL's approach differs from generic automation tools.
The platform deploys domain-specific AI agents that validate claims in real-time, automatically track policy changes, and predict denials before they happen.
Meet the Former Congressman Automating Healthcare
Denver Riggleman founded HOOTL in 2021 after careers in intelligence analysis and Congress.
The former Virginia representative who served on the January 6 Committee now applies his data science background to healthcare's messiest problem.
His regulatory connections give HOOTL an edge few startups can match. The company operates as RIIG Technology Inc. but brands its healthcare product as HOOTL—short for “Humans Out of the Loop.”
Why 5IR Funds Bet Big on Compliance-Aware AI?
This deal signals investor appetite for vertical AI in regulated industries. David Carstens, Founder and General Partner at 5IR Funds, emphasized HOOTL's unique positioning: combining AI automation with regulatory intelligence creates a moat that generic solutions cannot replicate.
5IR Funds manages a $200 million fund focused on Fifth Industrial Revolution technologies, including AI, blockchain, and quantum computing. The firm sees HOOTL as infrastructure for trust-based automation in healthcare.
HOOTL Funding Overview
Metric | Details |
---|---|
Funding Round | Series A |
Amount Raised | $6.5 million |
Lead Investor | 5IR Funds |
Founded | 2021 |
CEO | Denver Riggleman |
Previous Round | UAE investors (May 2025) |
Headquarters | Charlottesville, Virginia |
From Dental Pilots to Healthcare-Wide Rollout
HOOTL successfully tested its platform in dental practices, proving the technology works against both current and legacy systems. The company plans a broader launch across partner networks in Q4 2025.
The funding will accelerate product development, strengthen regulatory capabilities, and expand market reach. HOOTL's immediate challenge: scaling beyond dental into diverse medical specialties while maintaining its compliance edge.
Can AI Really Fix Healthcare Payments?

HOOTL's success depends on delivering measurable ROI—specifically reducing denial rates and accelerating reimbursement cycles.
If the platform proves it can consistently recover revenue lost to administrative friction, it becomes essential infrastructure for an industry desperate for solutions.
The regulatory relationships provide a defensible advantage, but execution matters most. Healthcare providers need proof that AI automation won't create new compliance headaches while solving old ones.
Find HOOTL
Platform | Link |
---|---|
Official Website | hootl.com |
RIIG – HOOTL | |
Legal Entity | RIIG Technology Inc. |