Dovetail is an innovative company with a talented, experienced team that knows the insurance business.

Our Past

Dovetail Insurance is built on the idea of insurance innovation. The company was formed in 2006 with the belief that there was a better, faster way to process insurance transactions. Dovetail’s technology platform was created, and combined with an experienced insurance operations team, and staff who are licensed, and understand insurance processes. The company — with backing by a New York-based venture capital firm — grew quickly, functioning as the virtual back office for carriers and managing general agents (MGAs). Dovetail performed all policy-related functions — from distribution to policy issuance and management — more efficiently than companies could do themselves.

Our Future

Dovetail’s business has expanded, and so have the opportunities for carriers and MGAs to use its solutions. With pressure on insurance companies to grow their businesses, Dovetail quickly recognized an opportunity to serve that need by expanding its services. Today, Dovetail’s insurance product delivery services help carriers, MGAs and brokers bring new products and programs to market quickly. Leveraging its unique, cloud-based solution, the company is really changing the way the insurance industry does business. Dovetail not only helps companies respond immediately to new opportunities, but helps them react effectively to market changes.

Our People

At Dovetail, understanding of insurance systems and processes is deep-seated. The company’s employees have extensive technology and insurance experience. That makes it easy for them to relate to carriers, MGAs and brokers, delivering services and solutions that have a big impact on their businesses. Innovation is also a critical focus at Dovetail where the company’s employees are always looking for new ways to service companies in ways no one else can.


We do what we say we’re going to do all of the time. Anything short of that and we’ve failed.


We depend on each other. It is impossible for one of us to succeed and one of us to fail. Success requires a team, working together.


We are driven to service our clients, and make them happy with what we deliver. We are always eager to exceed our customers’ expectations.

We have an experienced team with innovative ideas.

Rich Drab CEO
(803_ 255-8894

Rich Drab is focused on providing technology solutions that enable agents and carriers to easily come together to cover the risks of businesses, organizations and individuals. Rich has more than 25 years of leadership, consulting, and technology experience, primarily focused on the insurance industry. Before joining Dovetail, Rich was a Partner in IBM’s Global Business Services practice. Prior to joining IBM in 2012, Rich held several leadership roles at Rosetta, Sapient, and Accenture. Rich is a graduate of Loyola University of Chicago.

John E. Toole IV CIO

John Toole has a passion for building new technology platforms.  During more than 20 years in the insurance industry, he has seen that technology evolve from green screens to the latest technologies he’s working with today.    At Dovetail, he’s the primary architect for the company’s advanced product delivery platform where he oversees the development, systems security, backup and recovery for all client implementations.   He started his career at PMSC, held positions with InsLogic, and was formerly the CIO for Trumbull Services.

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Dovetail Insurance
1333 Main Street, Suite 600
Columbia, SC 29201
(803) 255-8891

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