Friday, May 22, 2026

How One Company Digitized the Medicare Enrollment Process


Medicare, Medicaid, CMS, Coverage

According to the data, as of 2021, about 64 million Americans are covered by health insurance Centers for Medicare and Medicaid Services. But about 70% of Medicare people don’t compare their plans during open enrollment, Kaiser Family Foundation established. Dave Francis, chief executive of insurer Healthpilot, said the process was confusing and slow, making it difficult for seniors to sign up.

“The way people get insurance today is stuck in 1975,” Francis said. “They either have to have someone come to their house and sit across the kitchen table and offer them a small portion of the plan from a handful of insurance companies. Or, they’re on the phone with someone who has a high-pressure sales orientation and they get a lot of information over the phone .”

Nashville based healthy pilotAs an insurance broker, founded in 2021, the company is trying to simplify the process with its AI-powered platform. Users can enter their location, doctor, prescription, pharmacy and the benefits they want on its website. Healthpilot’s AI will then offer the plan from the insurance company it thinks best suits that person’s needs. If users are satisfied with the proposed plan, they can sign up from the website. It also provides a phone number if a consumer has a question and wants to speak to a person directly.

Healthpilot’s AI uses data from anonymized medical records of about 2 million patients, Francis said. It takes a customer’s information and compares it to a group of similar patients to determine the customer’s health usage.

“Prospective utilization profiles based on customers — knowing who their doctors are, what drugs they take, which pharmacies they go to — allows us to go into their specific regional market and say, ‘this is the best plan for you’ “

The company also contacts users annually to confirm whether they are still on the plan that works best for them, Francis said.

“We have all your information so we can help you every year and get in touch with you and say, ‘Hey, you’re still on the best plan for you. You don’t have to worry about anything, just update. . . . ….or ‘Hey, we see you’re seeing a new doctor or you’re taking a new drug, and this Humana plan you had last year isn’t quite right for you now, but here’s another Humana plan that’s best for you ,'” Francis said.

For its services, Healthpilot then gets a commission from the insurance companies with which its users sign up, Francis said. The startup receives about $500 in commissions for the first year someone signs up, and then customers receive between $250 and $300 in commissions each year they renew the plan. Consumers do not have to pay for Healthpilot’s services.

To help clients understand their company, Healthpilot partners with financial advisory firms such as UBS, BlackRock and Charles Schwab. The companies sent email links to their retired customers and referred them to Healthpilot’s website. In return, the company tells the financial advisor the client’s health insurance plan of choice so that it can be included in their financial plan. Healthpilot has worked with about 20,000 retirees in the process, Francis said.

Other insurance brokers include go healthy, Choose a quote and American LifeBut Francis said Healthpilot differentiates itself from traditional brokers by digitizing the process and using an artificial intelligence platform to compare plans.

Francis added that the company hopes to go beyond insurance in the future, such as helping consumers with annual health checks, medicines and nutrition.

“finally, [wellness] It starts with health insurance, but as we build this relationship with our customers, there are more things that we can communicate with and engage with them,” he said.

Photo: Vadzim Kushniarou, Getty Images



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