Business Tips • Industry Insights • 36 minutes

Cybersecurity & Leadership: Protecting Your Business Inside and Out

April 29, 2025

Episode Overview

Chesapeake Electric COO Courtney Greeley has served in the United States Air Force, worked for the country’s National Security Agency (NSA) and been on the ground floor of cybersecurity startups.

She brings a military/tech background into the trades, and has strong feelings about both being a good manager and protecting your company from cyber threats.

“I lead with vulnerability because it shows that it's okay to make mistakes,” Greeley says. ” We want to learn from those mistakes.” 

She encourages others not to be afraid to make mistakes or to choose safe paths that don’t lead to growth.

“You get one life, so just take the chances,” Greeley says. “Take the risks. It could work out or it could not, but either way, you've learned something.” 

She also believes employees can tell if a manager isn’t being genuine with advice and directives.

“Leadership is about growing people and you can't fake that,” Greeley says. “You have to really care about people's growth.”

Along with being sincere, her experience has shown that company management also needs to be aware of modern tech problems, and already be ahead of the curve.

“There are a lot of ways to tackle cybersecurity,” Greeley says, “but the one thing you can't do is not do it.” 

A company that gets caught napping in this area will suffer consequences, she says.

“You have to wake up and take action on cybersecurity because this is the digital world,” Greeley says. “Anything that's connected is vulnerable, and it's your business.” 

Courtney Greeley recently joined ServiceTitan’s Jackie Aubel on the “Toolbox for the Trades” podcast, which included Greeley’s thoughts on:

  • [8:19] How to lead with values and create a no-toxicity workplace

  • [10:59] Working with end-users in the trades

  • [14:39] Why letting go of high-performing employees might be necessary

  • [15:29] How core values set culture

  • [25:32] Why cybersecurity is non-negotiable, but it doesn’t have to be overwhelming

To hear more stories from the trades, subscribe to Toolbox for the Trades on Apple Podcasts, Spotify, Google, or anywhere you get podcasts.

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About the Show

Toolbox for the Trades is a podcast where top service professionals share the tips, tricks, and tactics they use to succeed in their industry. Hosted by Jackie Aubel, this podcast is brought to you by ServiceTitan—the leading home and commercial field service software.

Episodes will feature stories and strategies to help contractors grow and scale their service business.

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