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Randolph Chestang IV, CEO and Founder on Notable Men

FOUNDER TO THE PROFILE

Randolph Chestang IV

CEO and Founder, CairnLedger

“I attribute my success first and foremost to God. I am thankful for His blessings, and He gives me the perseverance to never give up and never quit. Even when doors close in my face, I keep pushing forward, and I always find victory in the end because I want it and I believe it is meant for me.”

BASED IN
Washington, DC 20744
INDUSTRY
Tech

CONNECT

About

Randolph Chestang IV is the CEO and Founder of CairnLedger, a technology company that builds web applications for small healthcare clinics. The platform brings together data from electronic health records, billing, scheduling, and spreadsheets into one clear, easy-to-read interface, helping clinics operate more efficiently. He specializes in web applications and healthcare management, and he holds a concentration in public-private sector leadership.
A retired Navy commander and Surface Warfare Officer, Chestang began his naval career in 1999 and retired in 2022 after more than 20 years of leading teams, managing budgets, and overseeing complex operations at home and abroad. He later served as an Assistant Professor and Navy Chair at the National Defense University and then as Team Submarine Internship Program Manager at Serco, where he mentored more than 100 college interns. Over half of those who completed their degrees went on to secure full-time roles within Serco or Team Submarine. He currently serves as a Naval Project Manager at Booz Allen Hamilton. He earned a bachelor's degree in mechanical engineering from Southern University in Baton Rouge, a master's degree in national security from the United States Naval War College, and is completing an MBA at Johns Hopkins University, expected in May 2027.
Beyond his professional work, Chestang serves on the board of REACH Inc., supporting young people in building reading and writing skills, and he is a member of Omega Psi Phi Fraternity, Inc. His honors include the President of the United States Lifetime Achievement Award and a Father of the Year recognition. He credits his success to his faith in God and the perseverance it inspires, and he holds character, integrity, and family as the guiding values of his professional and personal life.

Key Areas Of Focus

  • 01. Web applications
  • 02. Healthcare management

IN HIS OWN WORDS

The Q and A

  1. 01

    What do you attribute your success to?

    I attribute my success first and foremost to God. I am thankful for His blessings, and He gives me the perseverance to never give up and never quit. Even when doors close in my face, I keep pushing forward, and I always find victory in the end because I want it and I believe it is meant for me.

  2. 02

    What’s the best career advice you’ve ever received?

    The best career advice I ever received was to always stay flexible and to bloom where I am planted. Wherever I am, I take the lessons that location offers and give my best effort, making the strongest impression I can while I am there.

  3. 03

    What advice would you give to young men entering your industry?

    Leadership takes courage, and it is not easy. You will need to listen, learn, be patient, and stay positive, because the path can be discouraging. Remain flexible, since things rarely go according to plan. Stay the course, keep pursuing what you believe will work, keep doing your research, keep believing in what you are doing, and never give up.

  4. 04

    What are the biggest challenges or opportunities in your field right now?

    My biggest challenges right now are getting the business off the ground and securing financing. Whenever you try to create change, things seldom go exactly as planned, so you must remain humble, patient, and positive. I hope to find an investor or some form of funding to carry out the next phase of my business.

  5. 05

    What values are most important to you in your work and personal life?

    The values most important to me are character, integrity, and family. I work hard to put my family first, but my character stands ahead of everything else. When you do things the right way, people will know who you are through your character and integrity.

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