Three years ago, in a pediatric oncology ward in Ontario, a woman signed up for a business networking group. Her son was in the middle of a two-year cancer battle. Her newborn was at home. Most people would have filed that under the worst possible timing. Kayleigh Kennedy has since called it a pivotal moment in her business growth.
The Coach Business Owners Call When the Plan Isn’t the Problem
Kayleigh Kennedy is the founder of Kayleigh Kennedy Consulting and the Acting Chief Executive Officer of The Entrepreneur Nation®, the referral network she first joined as a member from that hospital room. She has coached more than 200 entrepreneurs across five years, most of them owners who arrived holding a strategy that looked fine on paper and a result that had stopped moving. What she is known for is the part sitting underneath the strategy.
From Hospital Newsletters to Rooms Where Deals Close
Her first professional writing was a weekly e-newsletter at Cambridge Memorial Hospital, where she interned in communications in 2013 and set up the organization’s first official social accounts. She followed it with media relations at the Guelph Storm Hockey Club, liaising with Rogers Communications and Sportsnet during an OHL Priority Selection year. Then a marketing role at the Waterloo Region Record. Then a Bachelor of Public Relations from Conestoga College, layered on top of an earlier diploma in applied photography from Sheridan.
The through line was narrative. Public relations taught her that the story attached to a person or a business decides which doors open for it. Four and a half years as a marketing coordinator at OTIP, the Ontario Teachers Insurance Plan, taught her positioning: how a thing gets framed determines how it gets received.
Then she moved into sales and mindset coaching at an elite sales training firm, and the lesson sharpened into something she now treats as foundational.
Sales is really a transfer of belief. You cannot hand someone a conviction you do not hold yourself.
She closed over seven figures in sales in that period and earned six figures in commission. She also did it during the two years her son was fighting cancer, with a newborn at home. He won. The sales numbers and the hospital calendar overlap almost exactly, and Kayleigh Kennedy is direct about which one carried the other.
Mindset and belief carried me, and that created the motivation. I know it works because I lived it.
That period is why she now refuses the trade most business owners assume they have signed up for. In January 2024 she left her role at the previous coaching company (where she was already earning over 6-figures) to launch Kayleigh Kennedy Consulting on a premise she had already tested under the worst conditions available: you can have it all, the business and the personal life.
Eleven Members in Three Months, and a Chapter That Doesn’t Exist Yet
Her Acting CEO post at The Entrepreneur Nation® is a two-month contract, taken on to support the founder while she travels and builds overseas. A short runway forces hard prioritization, and Kennedy set three priorities.
The first is expansion. She is launching a brand-new chapter in a new city, extending the organization’s footprint past its current base. The second is her own chapter. As Senior Regional Director of the Guelph South Chapter, a referral group where each professional holds an exclusive seat for their field, she has grown membership to 11 in three months, across a summer, which is the season most networking organizations quietly write off. The third is a podcast. She has begun interviewing members and plans to launch in the fall.
She runs the organization the way she coaches, which is to say she picks the few moves that carry the most weight and declines the rest.
The client work follows the same principle. One case: a high-achieving professional with more than a decade in business, caught in repeating cycles of burnout that were reaching her team, her clients, and her family. The interventions were structural. She released clients and team members who cost more in stress than they returned in value. She raised her rates. She stopped punishing herself for being human. By the end of the engagement she was attracting significantly more aligned clients, with visibly more room and energy in her practice.
She believed she had to tolerate the stress to succeed. Once that shifted, everything else opened up.
Other outcomes take the same shape. An overworked, underpricing client now works fewer hours, earns more, and holds a client base that matches her values. A business owner who spent years chasing clients now attracts them, with revenue up and time returned to her relationships. A third arrived overwhelmed and unsure of herself, and left with something closer to steadiness.
Kennedy remains deeply connected to these outcomes, measuring success not just by increased revenue, but by building a business that stays true to core values.
The strategy was rarely the missing piece. The belief underneath the behaviour was.
Most of her clients built a business on one area of real expertise, then found themselves buried under everything else it takes to run one. She tells them it does not have to be that heavy. When you show up in your own authentic energy, selling and marketing your business stops feeling like a chore.
What She Went Back For
She joined The Entrepreneur Nation® from a hospital room because she knew she needed to connect with the right people to grow her business, especially when the rest of her life was on hold. It became pivotal to her own business. Now she is supporting the one running it,supporting expansion and also giving members across the Nation a new platform to share their voice and raise visibility for both the organization and its members, and the membership she once bought from a bedside chair has become the organization she has become a leader within.
The timing was never wrong. It only looked that way from outside.
Ask her what she coaches, and the answer is not a strategy. It is the thing a person has to believe before the strategy will work at all.
Kayleigh Kennedy is the Founder and Mentor of Kayleigh Kennedy Consulting and the Acting Chief Executive Officer and Senior Regional Director of The Entrepreneur Nation®, based in Guelph, Ontario, Canada. She works with entrepreneurs and business owners on the beliefs sitting underneath stalled growth, and has coached more than 200 of them over five years. To connect with Kayleigh or learn more, visit her LinkedIn Profile.
