Kevin Gregory

Kevin has degree in Accounting from the University of Cincinnati. For 20 plus year’s he has worked with insurance brokers, benefits consultants, insurance carriers, and affinity groups providing strategic planning, new product development and product distribution solutions.

Key projects:

Developed on-line employee benefits enrollment distribution channel enrolling over 250,000 employees and selling over $6 million in voluntary benefit premium.

Worked with personal training company to develop on-line, interactive fitness and wellness application.

Helped manage and grow a pharmacy benefit management (PBM) carve out program with over $600 million in annual spend.

Assisted individual health insurance carrier increase market share through strategic partnerships.

Program manager for affinity based health insurance program with over 25,000 small businesses covering more than 130,000 employees and over $700 million in annual premium.

Developed business model to the help the uninsured receiving grant commitments from Foundation of over $3.0 million.

Passionate about innovation, diversity, and small business entrepreneurship, Kevin is active in his community through volunteer work at the American Jewish Committee (AJC), Cleveland Bridge Builders, United Way, and Park Synagogue. He participated on the Governor’s Task Force for a Drug Free Workplace and launched Cultural LinksTM a diversity and leadership program for 10 – 15 year old students from diverse backgrounds for community development.

Kevin and his family live in Cleveland, Ohio.

Principal: Meet Richard Matthews

Richard graduated from Western Michigan University in 1968 with a degree in teaching. After 4 years in education he left the field to begin his insurance career with Equitable Life of New York.

He struck out on his own in 1984 to establish an employee benefit practice in the suburbs of Detroit, Michigan. In 1986 he established a specialty product with Cigna for ancillary benefits that fit perfectly with Michigan Blue Cross and Blue Shield. At the time BCBS has a “triple option” health product that was a perfect precursor for Defined Contribution plans. The combination of the BCBS health product and the Cigna ancillary plans allowed Richard and his new partners to lead the way for DC plans for companies with as few as 25 employees.

While DMCO enjoyed great success with the DC approach, it created substantial administrative headaches with the annual Open Enrollments. So in 1996 Dick jumped on the digital admin bandwagon with Employease and never looked back. In 2004 he sent everyone home to work at their own pace from their own homes. And again, neither he nor his staff ever looked back. Over the years DMCO has used a number of vendors including the aforementioned Employease, bSwift, benefitsConnect, and Accordware.

Dick (along with his wife Martha) moved to South Carolina in 1997 betting that the Internet would be the future of the insurance business - actually the future of any and every information based enterprise. It took a while to be sure, but now there is no doubt that a digital backbone is required for any agency that wants to survive and thrive in the 21st Century.

Dick now calls on agents that need guidance on moving their practice and admin services in to the digital age, with ACA compliance a real specialty.


Our great secret and significant advantage is that we do not have a minimum monthly cost for each agent client. Software companies may offer a very low PEPM (Per Employee Per Month) rate, but it comes with a monthly minimum that effectively eliminates the smaller employer. So our fee of $3 PEPM is charged against the exact number of people on the system. If the employer has 20 employees, the cost is $60 per month. If the employer has 40 employees, the cost is $120 per month, etc.

There is a one time account specific set up fee that ranges from $650 to $1000 depending upon the features of the case. The $3 PEPM fee includes full Cobra admin and my services in addition to the online enrollment and digital admin system.

In addition, by using the Humana products, the agent gets our automated enrollment services for just 30% of the voluntary worksite commissions, which is about one half of what most enrollment companies charge. 70% to the agent, 30% to DMCO.

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