Jonathan Comyn’s Approach to Building a Career Around the One Thing Leaders Often Overlook

Pressure has shaped nearly every chapter of Jonathan Comyn’s career. From law enforcement and emergency response to national leadership roles and entrepreneurship, Comyn has spent decades inside environments where decisions affect people in immediate, tangible ways. This experience now informs the work he is becoming known for: helping businesses scale without losing sight of the people inside them.

Today, Comyn operates as a fractional COO, entrepreneur, and author, while also working as the COO at Teen Business Academy, an entrepreneurship program designed for students from fifth through 12th grade. His professional reach spans operational consulting, leadership coaching, business development, public speaking, staff training, and cross-functional collaboration, but the ethos beneath it all remains consistent.

Comyn says, “It’s all about the people. You cannot have great customer service without great employees.”

This belief has become a defining characteristic of his work in the growing fractional executive space. Within the industry, he often observes that many operators lean too heavily toward systems, while many coaches stay too far removed from execution. Comyn positions himself in the middle, assuming the role of an operator and a leadership coach, while being deeply involved in the mechanics of a business and the development of the people running it.

“I’m not just the guy who’s going to get the work done. I’m the guy who’s going to coach and develop the staff, get people focused on the future, and help create buy-in to the company,” he says.

Long before entrepreneurship entered the picture, Comyn’s career began in public service. He spent eight years in law enforcement, eventually serving as a county emergency manager and volunteering in emergency response roles. The role, he recalls, demanded rapid decision-making and extensive staff training, responsibilities that later opened the door to the American Red Cross.

According to Comyn, he remained with the organization for 14 years, holding leadership positions that ranged from local operations to national training oversight. He managed programs involving CPR, first aid, learning to swim, and lifeguarding instruction while overseeing instructor quality and training delivery across the country.

Looking back, he sees a consistent thread connecting every phase of his career.

“Even when I was in search and rescue in high school, it was about helping people,” he says. “Teaching people how to help other people has followed me through my entire career.”

Comyn’s transition into entrepreneurship arrived after the COVID-19 pandemic reshaped his professional priorities and personal perspective. Years spent traveling nationally for leadership work had taken him away from home for long stretches, something he notes became increasingly important as his children grew older. An opportunity to join a smaller business in the car wash industry, he recalls, allowed him to remain closer to home while stepping deeper into operational leadership.

That period of extensive travel inspired his first book, The Traveling Dad, expected to be released this summer. Comyn presents the book as a project that focuses on the realities of leadership, family, accountability, and maintaining meaningful relationships while managing demanding professional responsibilities. “It’s a holistic approach to the individual,” he says. “How do you lead well, support your team, manage your responsibilities, and still take care of your family and friendships?” The book also marks the beginning of a larger public-facing chapter for Comyn, who plans to expand into speaking engagements focused on operational culture and entrepreneurship.

Much of Comyn’s current attention is now centered on Teen Business Academy. Comyn highlights that the academy teaches entrepreneurship fundamentals to young students while helping them launch real business concepts, something Comyn believes fills a critical gap in traditional education. “I saw an opportunity to make an impact for youth and make a difference in a lot of people’s lives,” he says. “I get to take everything I’ve learned over almost 30 years and help the next generation learn those lessons earlier.”

Comyn believes his mission rises to greater significance as conversations around AI and the future of work continue to accelerate. His second upcoming book, Leadership in the AI Age, examines how rapidly advancing technology is reshaping workplace dynamics and the emotional realities employees now face inside AI-assisted environments.

The book, he adds, opens the dialogue on responsibility. Comyn says, “We’re so fast to implement new technology without understanding the human cost of all of that. Leadership still requires human discernment.”

While systems and metrics matter, Comyn argues that sustainable businesses are ultimately built by leaders willing to invest in people with the same intensity they invest in performance.

Throughout the trajectory of his career, Comyn often returns to the idea that employees are not separate from the business. They, he emphasizes, are the business. “You can have high expectations for performance and still care deeply about people. I believe the strongest companies are the ones where employees feel supported and connected to the mission,” he says.

As Comyn prepares for the next phase of his career, including expanding his fractional leadership work, stepping into ownership, publishing new books, and entering the speaking circuit, his larger ambitions ultimately remain tied to creating organizations where people grow alongside the business itself.