The Tenure CEO and Techskis co-founder is bringing his experience as an entrepreneur, community builder and father into the 2026 race for mayor of Collingwood. For Jonathan Hillis, building has always been about more than business. The Collingwood entrepreneur has spent much of his career building companies, organizations, teams and community initiatives. Now, he is looking to bring that same builder mentality to municipal government as he campaigns to become the next mayor of Collingwood.
Hillis, the CEO and founder of Tenure and co-founder of Techskis, officially entered the 2026 mayoral race on August 21. He is one of four certified candidates running for mayor, alongside Yvonne Hamlin, Kathy Jeffery and Norm Sandberg. Collingwood’s municipal election is scheduled for October 26, 2026. His campaign is built around a straightforward idea:
“Keep Collingwood, Collingwood.”
The message speaks to a challenge facing a growing community. Collingwood is changing, but Hillis wants that growth to happen without losing the characteristics that make the town feel like home. His campaign describes the goal as preparing Collingwood for what is next without losing what makes it home. For Hillis, the issue is also personal.
“I’m a Collingwood entrepreneur, husband and dad to two young boys. My wife, Michelle, is a school teacher. We chose Collingwood to raise our family and have been actively involved in the community from day one.”
That family perspective is a significant part of how Hillis is presenting himself to voters. He is not approaching the mayoral race solely as a business leader or technology entrepreneur. He is running as someone who has chosen Collingwood as the place to raise his family and has spent years participating in local organizations and activities.
Hillis describes himself as someone who has always been a builder. “Family. Community. Teams. Organizations. Businesses. Better ways of solving problems.” That philosophy has shaped a career spanning technology, entrepreneurship, sports and community initiatives.
He is the founder and CEO of Tenure, and has also built BenchFund and Collingwood Eats. He is a co-founder of Techskis, a gathering that brings together founders, operators, investors and business leaders. Each venture has had a different purpose, from building technology and supporting youth sports to strengthening local businesses and bringing business leaders and investment into the Collingwood community.
“I’ve spent much of my career building things and bringing people together.”
That combination of entrepreneurship and community building is now at the centre of his political campaign. Rather than positioning his business background simply as a resume credential, Hillis is making the case that the skills involved in building organizations can also apply to running a municipality. The common thread is bringing people together, identifying problems and finding better ways to solve them.
Hillis’ entrepreneurial background is perhaps most visible through Tenure and Techskis. As CEO of Tenure, he has spent years working in the technology sector and building a company from Collingwood. Techskis represents another side of his work. The event brings together founders, operators, investors and other business leaders, creating a technology and entrepreneurship gathering in Collingwood. For a community outside Canada’s largest technology hubs, initiatives like these create another connection between Collingwood and the broader Canadian startup ecosystem. But Hillis’ involvement in the community goes well beyond entrepreneurship.
“Community and sport are a huge part of my life.”
He has been a member of the Optimist Club since moving to Collingwood and founded both the Collingwood Volleyball Club and Collingwood Flag Football. He also spends much of his time coaching local children in hockey, soccer and baseball.
That involvement gives Hillis another perspective on the community he is now campaigning to lead. His experience in Collingwood has not been limited to business events or the startup ecosystem. It has included youth sports, volunteering, coaching and raising a family.
The campaign’s message is centred on preparing Collingwood for what comes next while preserving what already makes the community unique. It is a familiar challenge for entrepreneurs. Growth creates opportunities, but it also creates new problems. Scaling a company requires infrastructure, people, resources and systems that can support what comes next. Communities face a similar challenge as populations grow and expectations change. Hillis wants to approach that challenge with the same practical mindset he has used throughout his career.
His campaign emphasizes three ideas: Listen. Build. Deliver.
The approach starts with residents, evidence, staff expertise and people closest to the problems. From there, the focus is on bringing people together and turning ideas into practical plans. The campaign ultimately emphasizes delivering measurable results and remaining accountable for them. That philosophy is consistent with the way Hillis describes his professional career.
“I’ve spent much of my career building things and bringing people together.” It is also reflected in his focus on community participation.
Rather than presenting himself as someone with every answer, Hillis is positioning the mayor’s role around bringing together the right people, understanding the challenges and building solutions collaboratively.
At the heart of Hillis’ campaign is a question that many growing communities are facing: how do you prepare for the future without losing the identity that made the community attractive in the first place? For Hillis, the answer starts with understanding what residents value about Collingwood. His campaign slogan, “Keep Collingwood, Collingwood,” captures that balance.
The goal is not to prevent change. It is to make sure change strengthens the community rather than erasing the qualities that make it distinctive. That includes the people, organizations, businesses, sports, recreation and community connections that have shaped Hillis’ own experience in Collingwood.
His background gives him a particular perspective on that challenge. As an entrepreneur, he has built companies.
As a community organizer, he has built organizations. As a coach, he has helped build teams. And as a father, he is now raising the next generation in Collingwood. “I’m a Collingwood entrepreneur, husband and dad to two young boys.” That may ultimately be the simplest explanation for why Hillis is making the jump from entrepreneurship into politics. He has spent years building things in Collingwood. Now, he wants to help shape what the community builds next.
Hillis’ campaign is now inviting supporters to get involved as it works to reach more residents, organize volunteers and build a campaign focused on listening, practical ideas and accountable results. Supporters can contribute through the campaign website, with donations helping the campaign connect with residents and build its grassroots efforts.
You do not have to be a Collingwood resident to support the campaign financially. Anyone who wants to support Hillis’ mayoral bid can contribute through the campaign site.
To learn more about the campaign or support Jon Hillis for Mayor, visit the campaign website called Jon Hillis for Mayor of Collingwood.
