Executive Management Team

Joe Kavanagh

Director, President and Chief Executive Officer

Joe is the President and Chief Executive Officer of Richmond National and a member of the Company’s Board of Directors. Prior to founding the Company in 2021, Joe had a twenty-five-year career in investment banking where he focused on public and private capital raising, new company formation, and M&A, exclusively in the insurance industry.

Joe began his insurance investment banking career in the New York M&A group of CIBC Wood-Gundy before joining the Marsh & McLennan Companies. Next, he helped start the insurance M&A effort at BHC-First Union Securities, later Wachovia Securities, in 2000. In 2003, he joined Friedman, Billings, Ramsey where he played a key role in developing and then leading the firm’s Insurance Investment Banking Group.

Joe earned his bachelor’s degree from Washington & Lee University and holds an MBA from the Stern School of Business of New York University.


Ashlee Randall

Senior Vice President and Chief Underwriting Officer

Ashlee is Chief Underwriting Officer of Richmond National. Ashlee has over twenty years of underwriting experience in the excess and surplus lines property and casualty industry. Prior to joining Richmond National, Ashlee served as Vice President of Kinsale Insurance Company, where she led the Commercial Property, Small Property, and Inland Marine divisions as well as led their Energy and Environmental division. Ashlee also spent time at James River Insurance in various underwriting positions. 

Ashlee earned bachelor’s degrees from Sweet Briar College and holds the Associate in Insurance Services, Commercial Underwriting, Surplus Lines Insurance, and Chartered Property Casualty Underwriter designations.

Doug Carson

Senior Vice President and Chief Financial Officer

Doug is the Chief Financial Officer of Richmond National. Prior to co-founding Richmond National, Doug worked for over twenty years in the investment banking industry where he focused on public and private capital raising, new company formation, and M&A, exclusively in the insurance industry.

Doug began his career at USAA before joining the capital markets group at the Federal Reserve Board and then the economic analysis group at Freddie Mac. He began his investment banking career in the Financial Institutions Group of First Union Securities, subsequently Wachovia Securities in 2000. In 2003, Doug joined Friedman, Billings, Ramsey where he held positions of increasing responsibility within the firm’s Insurance Investment Banking Group.

Doug earned his bachelor’s degrees from Trinity University and an MBA from the Fuqua School of Business at Duke University.

Aimee Venn

Senior Vice President and Chief Claims Officer

Aimee is the Chief Claims Officer of Richmond National. Aimee has over thirty years of claims experience working with Lloyd’s syndicates in the U.S., admitted carriers, and E&S companies. Prior to her tenure at Richmond National, Aimee served as U.S. Claims Coordinator at Ark Syndicate Management and at Markel Corporation as an Executive Claims Examiner in its E&S division. She held Senior Claims Adjuster roles at Utica National Insurance Group and Sentry Insurance Company.

Aimee graduated Bachelor of Arts degree from Randolph-Macon College, Cum Laude, Phi Beta Kappa. 

James Flajser

Senior Vice President, Chief Strategy Officer and Chief Risk Officer

James is the Chief Strategy Officer and Chief Risk Officer of Richmond National. James has over twenty years of experience focused on the insurance industry in areas including corporate finance, strategy and operations. Prior to co-founding the Company, James worked for more than fifteen years at Friedman, Billings, Ramsey and its successor entities, most recently serving as Director, Insurance Investment Banking.

James graduated cum laude with a Bachelor of Arts from Duke University.

David Vanalek

Senior Vice President and Chief Legal and Compliance Officer

David is the Chief Legal and Compliance Officer of Richmond National and serves as the corporate secretary to the Company’s Board of Directors. David has over twenty-five years of experience working in the property & casualty industry as an attorney and claims professional. Previously, David worked for over fourteen years at Markel, where he served in various claims leadership roles and ultimately as the Claims Chief Operating Officer. Before joining Markel, David worked in San Francisco and Chicago for almost nine years as a defense attorney specializing in litigated insurance claims, among others.

David graduated magna cum laude with a Bachelor of Arts from the University of California at Los Angeles, and earned his Juris Doctor from the University of California, Davis School of Law. David is an actively licensed attorney in Virginia, Illinois, California and Washington, D.C.

Alex Albro

Senior Vice President and Chief Information Officer

Alex is Chief Information Officer of Richmond National. Alex has over twenty years of experience in enterprise IT architecture, cloud infrastructure, software, security, and disaster recovery, including more than ten years within the E&S insurance and financial services industries. Prior to joining Richmond National, Alex spent time at Kinsale Insurance, James River Insurance, Capital One Financial, Ippon Technologies, and Adaptavist, where he architected cloud and enterprise IT solutions.

Alex earned a Bachelor of Science from James Madison University and is an AWS Certified DevOps Professional and Solutions Architect.

Jamie Bock

Senior Vice President and Chief Human Resources Officer

Jamie is the Chief Human Resources Officer of Richmond National. Jamie has over eighteen years of experience in human resources and corporate recruiting. Prior to joining Richmond National, Jamie spent time as the Director of Human Resources for the U.S. arm of Ippon Technologies. He also held roles at ICF International and Aerotek, Inc.

Jamie earned a Bachelor of Arts from Shippensburg University.