The surprising career trajectory of cyber investigations expert Cynthia Hetherington

From roadie to retail, the founder and CEO of Hetherington Group shares insights from her journey
VP, Education Strategy
Cynthia Hetherington, the founder and CEO of Hetherington Group
Cynthia Hetherington, the founder and CEO of Hetherington Group

Not many career paths follow a linear trajectory. Often, entrepreneurs find the best way forward is to leave room for the unexpected.

Cynthia Hetherington, the founder and CEO of Hetherington Group, is a perfect example. These days she spends her time tracking down and exposing vital data on national and international investigations into corporate due diligence and fraud. When she’s not knee deep in investigations, she leads the training of the next generation of investigators across public and private sectors, sharing her expertise in our increasingly data-intensive, cyber-focused world.

A born leader, Hetherington found her footing working behind the scenes with male-dominated rock bands. Later, when she became a librarian, Hetherington embraced technology early on and quickly became a sought-after collaborator by private investigators and law enforcement combing the then-newly emerging World Wide Web for data.

Hetherington shared a few insights into her career journey with NRF’s Susan Reda ahead of NRF PROTECT 2024. For the whole story — including a chance to learn the basics of open-source due diligence to avoid financial and reputational losses, and to hear her advice as a woman and entrepreneur in this niche — register for NRF PROTECT. The event takes place June 4 – 6 at the Long Beach Convention Center in Long Beach, Calif.

Can you tell us a little bit about the origins of your career?

I started my career as a librarian, but early on I saw the future of the internet and its impact on information dissemination, retrieval, use and storage. Seeing how technology was drastically changing the way we interact with information, I dedicated myself to learning about the internet, technology and all the associated functions. I started to incorporate the use of the internet and online databases into answering questions of my patrons.

Before long investigators and police heard of my skills and started asking for help with their own cases and research. What they were doing was much more interesting than looking up books about Marco Polo, so I started talking and sharing more with cyber cops, private detectives and specialist information users. My value as a librarian was immediate, and my knowledge of tech indispensable. Shortly after, I began apprenticing for an investigative firm out of Chicago called Five years later, I opened my own detective business. That was 25 years ago.

At what point did you realize you had the gumption to start your own company? What were the early years like?

I knew I was different from kindergarten. My teachers, parents, everyone called me out for leadership. I don’t know if I deserved that title, but I started to believe it, and it stuck. Before I even became a librarian, I was a stagehand working as an electrician and a lighting tech for rock bands like Guns N’ Roses, Rush and Van Halen.

As a young woman, too stupid to know she didn’t belong in an industry that was 98% male, I managed well. I was living independently by 18, working gigs at night, going to college during the day. I kept a chip on my shoulder to keep me tough around men who mostly intimidated me. I was there to work, not to flirt — I earned my check like the next guy. I operated on pure grit and determination. Those experiences served me well when I started my business. I’ve been learning ever since.

Growing up, do you recall being captivated by a crime show or a fictional character?

As far as the detective shows go, Scooby-Doo is the absolute bomb. Books are what really inspired me. Reading about the early philosophers — especially their math, theory and ideology — pushed me to try and discover a new path, science or ability.

A large portion of what you do involves training individuals and teams. What have you learned about people in this process and what have you learned about yourself?

Everyone learns differently. Some folks need assignments and practice by hand, others want to go off and learn on their own, reading and engaging in trial and error. Finally, some need to have me in front of them speaking on theory and method, catching each word as a pearl of wisdom. One certainty: All learners want to hear practical applications and expect to see outcomes during their classroom experience.

Are you more driven by the process or the result?

I’m absolutely process-driven. I can never refine my approach enough and am always driven to do better. Results bore me.

Conducting investigations can lead to some pretty uncomfortable, unethical and undesirable results. How do you leave the bad at the office and keep your spirits up when dealing with negativity on a daily basis?

I tell my team, my family, my customers, everyone … I am in the crisis business. It does no one any good if I fall apart when it matters most. Keeping cool during other people’s trauma is a delicate process of separating yourself emotionally while being engaged professionally. A pragmatic mindset is perfect for these delicate situations. Leaving that at the office is not a problem.

What challenges you most? What scares you the most?

Staying ahead of the curve as a subject matter expert means never losing your skills and not letting management and business ownership force you to set aside your vigilance of expertise. My fear is getting mired in business processes so deep that I forget why and how I do my work. However, being outdone by one of my students or employees is a proud moment because it means my investment is their benefit, and that’s just what we are about. Improving the next generation.

Do you have any hobbies you’d like to share? Peloton junkie or Orangetheory?

Like many analysts I’m a problem-solving puzzle junkie. I do a crossword puzzle a day. Also, a voracious reader and writer, I enjoy the written word, as any librarian would. When it gets down to serious fun, I like adventure sports like scuba diving, MMA and competitive anything.

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