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What We Do

Second Chair™ is a unique technology provider that helps companies impact better legal outcomes by leveraging more comprehensive information regarding the people involved each case.


Improving Decision Processes


The current deposition management process – focused on text and paper - is costly, labor intensive and delivers limited value to litigation managers. We believe that if “a picture is worth a thousand words,” then a video must be worth 10,000. Second Chair™ is founded on the principle that video depositions are both more cost effective and more valuable to litigation managers than text depositions.


The traditional current litigation process actually makes it very difficult for litigation managers to easily see the people involved in a case. Sure, they can read statements, Using Second Chair™ and seeing the witness testimony at your desktop,but that doesn’t provides a first hand impression of the witness any indication as to their demeanor, truthfulness and how they will be perceived by a jury. Second Chair™ technology makes it easy for litigation managers and their legal partners to see, share and store video deposition highlights.






Headquarted In Tampa, Florida

Expert Witness Testimony
Who We Are

The Second Chair™ team is well aware of the complex and costly nature of the litigation management process. Our team has spent the majority of their professional lives in the worlds of financial services, insurance, claims management, legal bill auditing and technology development.

Dennis Costello - President/CEO, Founder

  • 35 years of insurance industry P&C claims experience

  • CEO of Legalgard Information Solutions, Inc., acquired by PMSC, one of the first legal bill auditing companies to develop software for insurance claims litigation examiners

  • SVP and Chief Claim officer at Reliance Insurance Company for 10 years

  • Vice President Claim Administration and Finance, Chubb & Son, Inc.

  • BA Oakland University, CCLA

Keith Bogart - Chief Technology Officer


  • 25 years experience in Computer Technology/12 years in Law

  • Responsible for overseeing all aspects of the design, programming and implementation of the Second Chair™ software system.

  • Designed and implemented software systems for clients including Hillsborough County Clerk of the Circuit Court, Chase Manhattan Bank, GTE, NEC, and Teltronics.

  • Fluent and experienced in Windows, UNIX/LINUX, MSSQL, MySQL, Sybase, Informix, Oracle, C#, C/C++, Visual Basic, Delphi, Java, php, and ASP.NET.

  • BS in Statistics and Biometrics from Cornell University

  • JD from Stetson College of Law


Michael Conroy – Special Advisor


  • 38+ years executive claims, operations, strategic planning, due diligence and large scale project integration leadership

  • Principal, The Greyridge Group, providing broad based consulting to the insurance industry, law firms and self-insureds

  • CEO, WEMED Consulting, head of consulting practice for an international, New York based law firm

  • Executive Vice President, St. Paul Insurance, chief claim officer, chief administrative officer, chief privacy officer and chief ethics officer

  • Executive Vice President Claims and Administrative Officer Home Insurance Company

  • Managing Director, Senior Vice President for worldwide claims, Chubb & Son, Inc.

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