Founder | President - Collinqwood Volleyball Club
Jonathan Hillis is the kind of visionary entrepreneur who doesn’t just dream big—he takes those dreams and turns them into reality with a healthy dose of wit and grit. Jonathan’s mom might think he’s awesome, and his wife might have her reservations, but to his two boys, he’s a hero who deserves a spot on Forbes 40 under 40. And while that accolade might still be on the horizon, Jonathan’s mission is clear: revolutionizing access to education so that it’s less of a financial burden and more of an empowering experience for every student. With a career that reads like a playbook for startup success, Jonathan’s journey has been nothing short of extraordinary. As the Co-Founder and CEO of Tenure, Jonathan has been at the forefront of creating an innovative platform that tackles employee rewards, recognition, and retention head-on. His knack for understanding market needs led him to interview over 100 potential users, and in no time, he secured 10-20 clients for paid pilot programs. Not just a numbers guy, Jonathan’s leadership saw Tenure’s client base skyrocket by 40% in just one month, all while improving operational efficiency by 20%.
But that’s just the latest chapter. Before Tenure, Jonathan founded Payd Inc., where he masterminded a strategy to ease the financial stress of education for families and students alike. His efforts didn’t just resonate—they led to the integration of Payd’s solutions into educational frameworks across the board. Jonathan’s strategic vision and marketing acumen brought Payd to life, expanding its reach and securing the funding needed to thrive in the competitive edtech landscape.
Jonathan’s leadership isn’t confined to the boardroom. As President of the Collingwood Volleyball Club, he’s taken his passion for the sport and channeled it into developing young talent both on and off the court. His earlier stints as a coach at Mohawk and Sheridan Colleges underscore his commitment to nurturing future athletes, proving that his leadership extends beyond business.
Jonathan’s career began with a bang, from driving sales at Morcare International Insurance to breaking records at LivingSocial, where he led all of Canada in deals sold and revenue targets. Whether he was developing cutting-edge tech platforms or launching innovative marketing campaigns, Jonathan’s impact has been felt far and wide.
Through every role, Jonathan has maintained a clear focus: to build up others, solve human problems, and make education accessible and stress-free. His journey is a testament to the power of combining passion with purpose, and as he continues to break new ground, there’s no doubt that Jonathan Hillis is a name we’ll be hearing a lot more of—Forbes 40 under 40 or not.
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