Episode 3.08 – Jason Reynar – CAO of The City of Windsor

Jason Reynar

Rapidly improving our quality of life through local government innovation is Jason’s passion. As a lawyer and Chief Administrative Officer, he navigates through a haze of policy and regulation to find practical – sometimes disruptive – ways to deliver services, such as a public transit system powered by a ride-sharing app. Jason currently leads a team of over 3,000 dedicated public servants at the City of Windsor, Ontario, and is responsible to City Council for its nearly $1B annual operating and capital budget.  He strives to create an organization and community that is authentic, collaborative, creative and resilient.

Jason’s educational background includes a Bachelor of Arts (Honours) in Criminal Justice and Public Policy from the University of Guelph, a Bachelor of Laws and Masters of Law (Municipal Specialization) from Osgoode Hall Law School, and a Masters of Business Administration from the Schulich School of Business.  Jason is an Accredited Director with the Chartered Governance Institute of Canada.


CAO view of the region.

Tune in Thursday night at 7pm to hear the full conversation!

The first part begins with you, as we introduce you as the guest and your perceptions on the community/region you reside. 

  • Who are you? How did you end up CAO of the City of Windsor? 
  • You are somewhat new to the community so what are your “first-ish” impressions?How would you describe the municipality as a whole? 
    • What is working, and what is not, what are you building towards? 
  • What are your impressions about the region? 
    • How does the relationship work with Essex County administratively? Do you feel there is a right level of engagement, could be more or less? 
  • Finally, how does Windsor in your opinion fit into SW Ontario as a whole? 

The second part of the show we dig into more specific discussions. 

  • What is the role of municipal administration? 
    • You receive direction from elected officials but you (admin)are the experts. How does that direction get prioritized? 
  • Recently Windsor scored poorly on a democracy index for Ontario. Some of this is beyond administrative control – like the make-up of the council etc. How can administrative processes help impact local democracy, trust, and engagement?
    • Locally in Windsor there have been some issues that some in the community feel are rushed, or not properly engaging before a decision is made. 
  • I believe Windsor just passed a work from home pilot process. What does work from home look like for a municipality? Certainly some taxpayers might say “You are public servants, why aren’t you at your desk?” 
    • Does this open the door to work from anywhere? Is this a pathway to a new round of municipal outsourcing?
  • Can municipal administrations keep up with a rapidly changing world? The speed in which the world is change, is getting faster, and the relatively risk averse space that is municipal government makes it hard to innovate.
    • There seems to be a feeling that Windsor is playing catch up in this space where other SW Ontario municipalities – From this podcast conversations:
      • London’s multiyear budgeting that was credited with a $10M surplus that could be invested with affordable housing; 
      • Collaboration networks in Guelph-Wellington and the municipal leadership that is driving it is allowing them to Leverage Smart Cities funding to realign their economy. 
      • City of Kitchener repurposing an existing tax levy to fund a $100M+ small business/venture capital accelerator.  
  • If you could wave a policy magic wand, and change policy at the municipal, provincial or federal level, what would you change? 

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