An Engineer in the CEO Seat: Navigating Leadership as an Introvert

At BuildGroup, we often debate what makes an ideal CEO for a growth-stage company. Great CEOs excel in team leadership, customer-focused culture, vision-casting, strategy and product definition, efficient growth, and balancing profitability with growth. But one important lesson I’ve learned is that every strong CEO brings their own ‘special sauce’; there is no single path to success. Jeremy Gehring, the CEO of one of our portfolio companies, Cybrary, was recently promoted into the role and has been leading with excellence. I think you'll enjoy reading about his leadership journey from self-identified ‘introverted engineer’ to effective leader. I'll let Jeremy take it from here.

- Klee Kleber, Co-founder, BuildGroup, Executive Chair, Cybrary

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I started my first business when I was young, driven by a love of problem-solving and building things. What began as a small venture soon grew beyond my wildest expectations, and with that growth came the need to hire more people and take on larger responsibilities. Suddenly, I found myself in charge of leading an entire organization. It wasn’t something I had planned for – I never saw myself as a traditional leader; I was simply an engineer with a head for business, and I stepped into the role because the company needed someone to steer the ship. 

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Running a business, though, is a different kind of challenge, especially for someone like me – a self-professed introvert who thrived working quietly in a dark basement. Leadership required constant human interaction, a far cry from my natural comfort zone. In fact, by today’s standards, I’d likely be considered somewhere on the spectrum. Social interactions, negotiations, and people management were not skills I was born with, but as the company grew, I realized something important: for my business to succeed, I had to grow too.

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So, I approached leadership the same way I would tackle an engineering problem: that is, methodically and systematically. I took public speaking classes, devoured books on communication and leadership, and built a toolkit of strategies to manage complex social dynamics. For those naturally gifted with charisma, this might have seemed unnecessary. But for me, it was crucial. I relied on flowcharts, frameworks, and structured approaches, applying the same principles I used to solve technical problems. I adopted a leadership style rooted in transparency and candor, heavily influenced by Kim Scott’s concept of “Radical Candor.” I realized that people, like any system, can be managed with the right tools and approaches.

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After growing my company for over 20 years, I successfully organized its sale. It was a bittersweet moment –  I was proud to have built something from the ground up, but it was also time for the next chapter. I took a brief break but quickly realized that I don’t do well in retirement. I needed something meaningful to throw my energy into. That’s when I found Cybrary. 

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Initially, I joined to lead the engineering organization, fully content to leave the weight of running the company to someone else. But, as always, I couldn’t help but dive in headfirst. When I was asked to step into the CEO role, it wasn’t something I took lightly. It was an honor to be entrusted with the future of such an incredible company, but it also presented new challenges. 

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Leading Cybrary wasn’t just about solving technical problems; it was about guiding people, making sure the company thrived, and fostering a culture that empowered everyone. I’ve come to deeply value the importance of people and connections – something I didn’t fully appreciate in my early years as a founder. Diverse groups of people don’t just add value, they are the lifeblood of any successful organization. They bring fresh perspectives, new ideas, and a collective strength that drives innovation.

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As a CEO, I’ve learned that it isn’t all that different from being an engineer. You’re constantly faced with variables, unknowns, and challenges. The difference is that, while code is logical and predictable, people are not. Managing them requires a whole new set of tools. But, like with any engineering problem, I’ve found that if you apply the right frameworks and take an iterative approach, you can lead effectively.

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This journey has taught me the power of iteration, not just in technology, but in leadership and life. I’ve learned that it’s okay to admit that you don’t have all the answers. You experiment, adjust, and improve over time. The key is to approach every challenge with an open mind, to value the people around you, and to never stop learning. In leadership, as in engineering, there is always room for growth and optimization. 

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Looking back, I see that my introversion didn’t hold me back. It gave me a unique approach to leadership. And now, at Cybrary, I’m more motivated than ever to apply what I’ve learned to ensure the company’s success. It’s a different kind of problem to solve, but it’s one I’m proud to tackle, step by step, iteration by iteration.

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Cybrary is the premier cybersecurity professional development platform, providing the collective knowledge of the industry’s top experts and leading organizations to equip IT and security professionals with both the knowledge and skills to achieve their career goals. Recognized as an industry pioneer and innovator since 2015, Cybrary has grown its cyber-focused community to nearly 3 million users, including multiple Fortune 100 companies. BuildGroup currently invests in Cybrary.

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The information in this blog post is provided in good faith without any warranty. It does not constitute investment advice, recommendation, or an offer of any services or products of BuildGroup Management and it is not intended to provide a sufficient basis on which to make an investment decision. This document is provided for educational purposes only. Discussions of current or former BuildGroup portfolio companies are intended for educational and discussion purposes only. Any portfolio company so discussed has been selected based on objective, non-performance based criteria.

This content does not constitute or form part of an offer of any investment advisory services of BuildGroup Management, LLC, nor does it constitute or form part of an offer to issue or sell, or of a solicitation of an offer to subscribe or buy, any securities or other financial instruments, nor does it constitute a financial promotion, investment advice or an inducement or incitement to participate in any product, offering or investment.

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