Keenan Skelly joins LeaderSpeak to discuss moving from military and government service into cybersecurity entrepreneurship. The conversation explores startup culture, educational games, the challenge of switching between creative and analytical work, and why founders need both conviction and the right people around them.
Keenan has worked across personnel, physical, and cybersecurity. She served in the US Army as an explosive-ordnance-disposal technician and later worked at the Department of Homeland Security, where she led comprehensive reviews within the Office of Infrastructure Protection. That work included vulnerability assessments and exercises involving critical-infrastructure assets.
Her roles have included co-founder and CEO of shyftED, president and CEO of Spark Security Solutions, strategic adviser, board member, and adviser to organisations supporting women in cybersecurity.
Guest link: LinkedIn
Keenan’s experience spans the military, government, private contracting, and startups. Large bureaucratic organisations taught her what she valued and what slowed useful work. Starting a company offered the opportunity to shape the culture, choose the people collaborating on a problem, and remove processes that obstructed progress.
That freedom does not remove complexity. A founder creates the environment in which work happens and must decide which habits, partners, and expectations belong in it. Culture is not an afterthought; it begins with those early choices.
Keenan’s venture adapts a game that can be played in many settings to teach basic cybersecurity skills. Her earlier gamification work focused on technical audiences, while this effort is meant for everyone—from children to grandparents.
She sees broad education as necessary because people of every age use online shopping, social media, and other connected services. If the industry wants to reduce attacks that exploit human behaviour, basic security learning should begin early and continue throughout life. Games can make unfamiliar material easier to understand and remember.
Coffee and a written task list provide the start of Keenan’s day, but startup work rarely respects the original plan. New issues continually compete for priority. She also has to separate different modes of thinking. Accounting and profit-and-loss work demand a very different mindset from product creativity or sales ideas.
Rather than moving constantly between those modes, she tries to create space for each. Her description shows that managing energy and attention can be as important as managing the list itself.
Keenan’s first career lesson is to remain hungry for knowledge and experimentation. Cybersecurity offers many possible paths, and people often discover the right one only by reading, taking a course, or trying the work. Learning must continue after landing a job because the field changes quickly.
At the same time, she cautions against excessive self-criticism. Nobody executes every part of a career perfectly; most people are still figuring things out. Asking for help is part of progress, not evidence of inadequacy. She also normalises changing careers repeatedly: a person can move from bomb disposal to an entirely different professional life when circumstances and interests change.
For an early startup, the close team is only one part of the human environment. Investors and major partners should also represent the brand and culture the founder intends to build. Their influence can shape the venture long after an agreement is signed.
Pitching inevitably produces conflicting responses. Some people will dismiss the idea, while others will see its potential. Keenan advises founders to listen, prepare for setbacks, and still maintain conviction in the product they believe can create meaningful change.
