Who's Who of Professional Women


Ashlee Randall

As the senior vice president and chief underwriting officer since 2022 at Richmond National, a Virginia-based insurance company with nearly 100 employees, Ashlee Randall is a busy, seasoned expert in risk assessment, overseeing all underwriting functions and product lines, seven related departments, and the service division while working with the division manager, information technology, and the claims staff to stay on top of issues. Citing her growth at Richmond National as her greatest professional achievement to date, Ms. Randall is the top entry point person responsible for all underwriting submissions, getting policies issued, and ensuring great customer service while assisting with marketing efforts and representing the company at major industry events that she coordinates.

Extensively credentialed in her industry, Ms. Randall holds several key certifications from The Institutes Knowledge Group at the American Institute For Chartered Property Casualty Underwriters (AICPCU) and earned a Bachelor of Arts in mathematics and history from Sweet Briar College, graduating magna cum laude.As a published scholar, she co-authored the 2002 abstract “Low-Frequency Radio Transients in the Galactic Center,” in The Astronomical Journal. An insurance career veteran before joining Richmond National, she held several executive positions for four years at Kinsale Insurance Company and started her career working for three years at James River Insurance Company when it was a startup. At Kinsale Insurance, Ms. Randall established the energy division and managed the environmental division before taking charge of the company’s property and inland marine segment as vice president within a year. Since then, she has brought her vast network of contacts in the property casualty space to Richmond National, the third startup she has helped to grow and become successful, increasing the company’s ability to write more business and broaden its recognition.

Ms. Randall acknowledges, however, that in general, being part of startups can be challenging. Particularly with Kinsale Insurance, she recalled, the company started “in a very soft market” in the insurance arena, facing immense competition and making it more difficult to write new policies. Yet the company and she stayed on course, worked hard, and persevered. Her mentor Diane Schnupp, a former Kinsale executive, was especially helpful in answering any questions and was always very encouraging. In the early days at Richmond National, she said, it was “very much all-hands-on deck” where everyone was willing to help wherever and whenever they were needed. Ms. Randall’s track record of persistence is only part of what she believes is responsible for her own success. She also attributes taking chances, learning to invest in herself, good problem-solving skills, being flexible, valuing coworkers’ team efforts, providing training, enjoying working with people, and finding opportunities for career advancement—all of which helped her gain confidence over time.

To stay professionally current, Ms. Randall regularly reads industry publications and consults with the Richmond National chief legal officer, who helps her create policy forms as new insurance laws are passed. She is a former member of Chief, a private membership network for women executive leaders, and a past board member of the Richmond Chapter of the AICPCU. As an authority herself, Ms. Randall keeps colleagues up to date, gives presentations, and has been invited to be a featured speaker in September 2023 at the “Risk360” Risk Management Conference in Chicago, Illinois.  

Within the next five years, Ms. Randall hopes to help Richmond National expand to become one of the most successful companies in the region. Personally, she plans to keep moving forward, learning, and broadening her skill set, motivated by the desire to do well for her children, Reese and Kieran, and to make them proud. In her leisure time, she enjoys horseback riding and gardening.


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