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Tampa tech company pivots to services as it works to disrupt the health insurance industry

Margie Manning



Bobby Leesman, founder and managing partner, Enrollment Alliance

Workers faced with a wide range of confusing choices about their employer-covered health insurance could get help from a Tampa company that wants to make the purchasing process faster and easier.

Enrollment Alliance combines technology with a dedicated benefits advisor so employees can compare costs and enroll with carriers instantaneously, said Bobby Leesman, founder and managing partner.

The company initially launched five years ago with software designed to speed the enrollment process, but pivoted to focus on services as newer software displaced its own product. Now, Leesman said, Enrollment Alliance blends technology with services.

“We’re on the cutting edge of technology in health insurance, but at the end of the day consumers shouldn’t be left just to rely on technology to make one of their most expensive buying decisions. Next to their mortgage, health insurance is often the most expensive line item. Just clicking on some website and trying to decide those things for yourself is not practical,” he said. “We utilize technology to make it more streamlined and more accessible, but don’t ignore the fact that someone would love a consultant to help them through that process. That’s the space that we’re playing in.”

Since Leesman started Enrollment Alliance five years ago, it has grown to just under 50 employees. The company has offices in Atlanta and in suburban Denver, with the tech team and back office operations at the Tampa headquarters. Leesman is looking to add offices in Texas and the Midwest.

Enrollment Alliance works with 50 to 60 insurance brokers who make introductions to corporate HR departments. The company currently handles enrollments for more than 2,000 companies nationwide.


Corporate human resources departments often are overwhelmed during the annual open enrollment period, Leesman said. Enrollment Alliance sends a team of benefits advisors to the company to work with the HR department to manage the process.

“When they partner with us we create a dedicated communications strategy of how to first get employees to take action,” he said. “Instead of just emailing them, we use text messaging and email and we create follow-ups where they are able  to book a meeting … They get a text from us saying open enrollment is coming up, you are going to meet with your dedicated consultant, click here to pick a date and time and schedule your meeting.”

Then, instead of directing employees to a website with an array of choices, the benefits advisors walk each worker through the process.

“They don’t have to figure it out themselves,” Leesman said. “Instead, they are sitting next to an expert in the industry who can help them figure out questions and provide advice to design a package that fits your needs and budget.”

The benefits advisors consult with workers during companies’ annual open enrollment period, as well as with workers who are joining a company and need advice on health insurance. They also help HR departments learn how to coach workers on being better consumers of health care.


Leesman has a background in technology and when he founded Enrollment Alliance, he  developed software, dubbed Bolt, to speed the enrollment process. At the time, Leesman said, the insurance industry was “a dinosaur,” and it often took employees an hour to fill out all the paperwork needed for their annual health insurance purchase.

His software cut that time dramatically, by collecting an individual’s vital information one time and then mapping it electronically to a pre-filled PDF for all of the insurance carrier applications. “Suddenly you didn’t have to fill out all those applications,” he said. “We were able to smash down what would take an hour to 10 minutes.”

But newer technology was developed after Leesman introduced Bolt.

“What’s gotten so much more advanced is these new technologies have partnered at a high level with insurance companies. There is no paper application that transpires, it’s a data file coming out of the system … and as the information is collected it is transmitted to the insurance carrier in real time,” he said.

Enrollment Alliance pivoted. Instead of being a technology company, Leesman decided to focus on service.

“Bolt was my baby. It taught me so much. But you have to recognize where the market is going and I did quickly. It gave me a lot of skills to understand these new technologies much better than any of our competition does,” he said.

Going forward, he said the company will continue to focus on improved communications between HR departments and employees during the open enrollment period, displacing lengthy group presentations with text messages and videos.

“I speak to my clients a lot about the evolution of communication,” Leesman said. “We have this magic machine in our hands and no one is taking advantage of that in our industry. We are able to text an entire population of employees and tell them everything they would have learned in that 45-minute presentation, we deliver to them on their cell phone and email … They can watch a three-minute video to understand what’s changed with their insurance this year. They can text back and forth with a real person if they have questions leading up to enrollment. If they want to  gather information prior to us going out in person and sitting with them, we have live chats. Those are the things we’re focused on that that our industry has not been exposed to at this level.”

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