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Jack Esselen Named One of the 10 Most Empowering Leaders of 2023 by Industry Era Magazine

Updated: May 5, 2023

Jack Esselen, CEO & Founder of Sentry MD, is the leader of an innovative technology and service team that is transforming how its clients administer health record management for employees and students. Jack’s collaborative management style and mentoring derived from hard-won business lessons over decades keeps his team focused on continually improving internal operations and the user experience for clients and their members.

We take the hassle out of managing member medical files. Our health record professionals do the work and manage compliance.

The pioneering trailblazer began his career in the software industry. He learned how technology could enhance every aspect of business operations and often propel organizations to the forefront of their industries by disrupting status quo methods and practices. In all his leadership roles, Jack has leaned heavily on the ongoing development of software to accomplish business goals. His philosophy is to get machines to do as much as possible so we do only what humans can do and have fun. He is inspired by leaders who encourage a working environment where employees at all levels have a say and are motivated to contribute in significant ways to the mission and success of the company. Mistakes that are made along the way are managed as opportunities for improvement. The team determines how and why things go wrong and devises methods to enhance performance, leveraging the company’s significant investment and focus on technology.


At the outset of his career, Jack had the good fortune to join a small software company with six employees, McCracken Computer, that grew to be one of the largest and most successful technology companies in the insurance industry. With the support and leadership of his boss and founder, Frank McCracken, Jack played a central role in the company’s development and became one of three owners.


“At the crest of a wave of growth at McCracken, we had unhappy customers. The founder, Frank McCracken, called a meeting of all 160 employees at the time. We crowded into a yet to be furnished conference room, noisily at first, quieting down quickly, sensing the mood of our leader,” explains Jack. “This gathering was not a party, like so many we had enjoyed together. Frank’s speech was very short. He said: There are two things that are important in business. The customer (pause). And all of you (pointing to us — pausing again). In that order. That is all Frank had to say, so we disbanded knowing all our jobs were on the line for the customers. This is a lesson I never forget and bears on every business decision I make.”


Jack has been taking the company to new heights with this brilliant mindset. Sentry MD aims to eliminate the burden of processing member health forms and tracking compliance. Sentry MD processes all member forms within 48 hours of submission, even during peak periods. Once forms are submitted, members receive an email explaining their compliance status and other requirements that still need to be met. Reminders are sent to all members on a schedule determined by client institutions, highlighting conditions that have fallen non-compliant and those that will be expiring. Members and client administrators have 24/7 online access to account compliance status for each requirement and the history of all activity, including submissions, reminders, and logins. Additionally, client admins can run compliance reports for groups they are tracking.


For instance, one of Sentry MD’s largest clients switched from another method of tracking requirements and provided the company with their tracking data to load into Sentry MD’s system to get started. The prior system reported over 85% compliance. “When we ran compliance reports on their data in our system, compliance rates dropped to under 30%. The reason for this is our system, using CDC compliant rules designed specifically for tracking each client’s requirements, is far more accurate than other systems,” explains Jack. “Our clients have the peace of mind knowing our system accurately reflects the actual compliance of its members and provides them the information and tools to improve and maintain compliance.”



Sentry MD is continually enhancing its services and technology. Recently, it added a history tab to its inquiry program used by members and client administrators. All activity is reported, including document submissions, reminder notices, logins, and changes in compliance. “This greatly enhances understanding the overall status of each account. Another revolutionary enhancement slated for later this year is to track multiple sets of requirements for each member. This will streamline how we handle members who have multiple roles or who work at multiple clinical sites with different requirements,” elucidates Jack.


Finally, Sentry MD’s integration capabilities, including SSO, API and file exchange software, enable clients to display compliance data on client systems, as well as provide access to Sentry MD systems from a single sign-on from those same host systems. These integrations greatly enhance and simplify the user experience for all employees, students and administrators.

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