Overtime Names Caylon Cannon Head of Healthcare Revenue

Posted on:
August 5, 2026

Healthcare industry veteran joins Overtime to grow its first-party collections business and expand across the revenue cycle

Miami, FL — Overtime, a voice-first AI platform for billing, collections, and debt recovery, today announced that Caylon Cannon has joined the company as Head of Healthcare Revenue. Caylon will work with healthcare organizations and industry partners to grow Overtime’s first-party collections business, launch early customer programs, and help shape the company’s approach to the healthcare market.

Overtime sees first-party collections as the starting point for its work in healthcare. Patient receivables offer a clear opportunity to help providers recover more revenue and lower costs while making billing less frustrating for patients. From that foundation, Overtime plans to support more of the healthcare revenue cycle over time.

Caylon brings nearly four decades of experience in healthcare, revenue cycle management, and receivables. Most recently, he served as Chief Growth Officer at Somatus, a value-based care company focused on improving outcomes for people with kidney disease and other chronic conditions. Before Somatus, he was Chief Strategy Officer at Capio, a healthcare asset management company that helps providers improve cash flow and resolve patient accounts. At Capio, he led strategic partnerships and client relationships and helped advance a more digital, patient-centered financial experience.

He has also held leadership positions at DaVita Labs, Qualink-OSI, HCA Healthcare, Prisma Health, formerly Palmetto Health, and Orlando Health.

“Patient billing is one of the most frustrating parts of the healthcare experience,” said Dan Kutchel, CEO of Overtime. “People want clear answers and a simple path to resolution, while providers need to recover revenue without adding more cost and complexity. First-party collections gives us the opportunity to solve both sides of that problem. Caylon understands this market and will help us improve the patient experience, deliver measurable results for providers, and build from there.”

Caylon joins a growing Overtime team that includes experienced leaders from collections, healthcare, compliance, financial services, and technology. The company continues to build its platform with industry experts who understand the work firsthand.

“I’m excited to join a great team working at the forefront of voice-first AI,” said Caylon. “Healthcare organizations need better ways to manage first-party collections while treating patients with respect and making the financial experience easier. I look forward to working with our customers and partners to solve that problem and build toward a broader vision for the revenue cycle.”

About Overtime

Overtime is a voice-first AI platform for billing, collections, and debt recovery. Built by experienced industry operators and AI engineers, Overtime helps healthcare organizations, agencies, debt buyers, and other receivables teams recover more revenue, lower their cost to collect, and engage consumers compliantly.