Jason McKeen’s professional journey is a testament to his resilience and hard work despite years of personal hardships. By continuously pushing his boundaries, Jason built a legacy that stands on his own values. Navigating an unstable career, he made his way to chair BlackSwan Cyber Group, not only as its Co-founder but also as the CEO. As an introvert, it was one of the biggest challenges for Jason as he needed to support an organization, be its face, and become all that he never wanted to be. Redirecting his aspiration of becoming an architect or designer toward founding a cybersecurity company was the biggest change in his career trajectory, which earned him the title of one of the Most Influential CEOs to Watch 2025 by The CEO Views.
Finding the Silver Lining
Born on a military base, Jason lived a traumatic and unaided childhood of family abuse and hopelessness. Becoming a CEO or anyone of importance was never a thought or aspiration for him. Despite the roadblocks, Jason wanted to become a better person—someone his future kids could look up to. “I grinded it out every day, worked hard, and worked for some good and not-so-good organizations/managers,” shared Jason. In February 2025, Jason and his wife embraced their biggest dream and greatest risk by dropping his career and building BlackSwan Cyber Group. Without any safety net or support, they not only went all-in, but Jason also went on to become the company’s CEO.
An Academia of Excellence
Jason has always been a hardworking student during his high-school years. He worked to obtain good grades and created an opportunity to pursue further education through scholarships in wrestling. By the second year, he was already a provincial champion, national champion, and junior Olympic medallist. However, during his nationals, a hernia surgery changed his course of life forever.
While living couch to couch and figuring out life, he was offered an opportunity to work at an agricultural warehouse, where he learned everything about controls, governance, dispatch, and organization. Jason’s life pivoted when someone picked up on his analytical nature, which led him to pursue his Specialist Diploma, marking the start of his career in Information Technology.
After moving to Saskatoon for a job and having no plans other than to start building roots, he gained experience in multiple industries, including electrical, financial, government, industrial (OT), and consulting. Jason continued to obtain industry certifications and acknowledgements before establishing BlackSwan Cyber Group.
A Leadership Principle of Work-Life Balancing
Instead of fostering a “work-family” mindset, Jason shaped BlackSwan Cyber Group into a powerhouse of high achievers. The team is driven to deliver excellence on every project. Here, work-life balance is more than a buzzword—long hours are discouraged so employees can recharge and return with full energy. Jason goes a step further by limiting after-hours communication, encouraging staff to truly disconnect and enjoy personal time. On the rare occasions when work spills over, everyone understands the urgency and steps up without hesitation.
Leading Without Competing
BlackSwan Cyber Group was founded on the principle of building relationships, and the company still holds on to that principle. From the beginning, Jason decided that he was not going to compete with other companies. “I don’t believe you will ever win in this competition, and for that reason, I don’t work alone,” shared Jason. He ensures that his employees are the best, and the company partners with other organizations that share the same values. These organizations specialize in their field to expand BlackSwan’s value. Jason strongly believes that partnerships moving forward will provide a new foundation in the cybersecurity industry.
Ensuring Long-Term Success
As the CEO of the company, Jason started with a plan and vision, making sure they strictly remained attached to the company values. When it comes to ensuring long-term success of the business, he is extremely cautious about not delivering advice, services, or products that do not align with the company’s values or can change the hard-built work culture at BlackSwan Cyber Group.
What Today’s Leaders Must Possess
According to Jason, the ability to show one’s value is crucial for today’s leaders. Leaders must keep the staff informed about who and what they are working for. He believes that if leaders can value their employees and their work, they will not only work harder and be loyal to the leaders, but will also strive to develop themselves more if they have someone to look up to.
To Be the Go-to Person
When asked about what could be the best manifestation of himself in a few years from now from his present position, he confidently replied that he wants to be the person to work for. He wants to be able to pick up the phone, call someone, and ask if they want to work with him—and they are on their way. Jason wants to develop that culture and gain the respect of his peers. Not expecting it to be given, Jason is building a team, a community, and working to garner respect from the industry.
Being the Guiding Light
To date, Jason still does work that he does not necessarily enjoy, even though he does not always ace it. As a leader, he does that to support the staff who grind every day and to teach them the value of the work they do. Many people forget that those small things really matter to some people.
“We are here for support and to assist in a long journey that is developing, known as cybersecurity.”
