Creating a transformation. Digital Main Street celebrates 5 years of helping small businesses adapt.

by Darryl Julott   |   June 14, 2021   |   Share this:  

It’s hard to believe it has been 5 years already, but it’s even harder to imagine that is has only been 5 years. It seems like time slows down when you are driven by a mission and a passion, and that’s exactly what Digital Main Street is and has been for so many over the last 5 years. What started in 2014 as the founding team of John Kiru, Chris Rickett, Nirvana Champion and others has transformed into hundreds of team members across the province and country, tens of thousands of businesses having been supported, and a fundamental mission driven by a mutual desire and passion to help our small business community grow through the adoption of digital tools and technologies (a stance that has only been greatly accelerated over the last 18 months).

Everything starts somewhere

Every great idea begins somewhere. A conversation, a meeting, a presentation, somewhere. In the case of Digital Main Street, our origin is very reflective of our team, mission, and collective passions. In late November 2014, John Kiru (Founder of Digital Main Street and Executive Director of TABIA) met with Chris Rickett and Mike Major from the City of Toronto to explore a deeper partnership and further methods of support for small business owners across the City.

During this meeting which would be the catalyst for moving forward with Digital Main Street and making it the industry leading program it is today, the idea did begin somewhere. It began on a restaurant napkin as part of a conversation. Like everything new, all there was this night was an idea and a belief that this program could be the missing link for supporting small businesses across the city. From there, the hard work began and 18 months later Digital Main Street was launched on June 13th, 2016.

“Almost 7 years ago, a crazy idea I had was tabled around providing small businesses in our Toronto BIAs with digital transformation support to help bring them into the 21st century. We realized very early on that the future was no longer “bricks or clicks”, it was clearly going to be “bricks and clicks”. In the 1,825 days that have passed since we launched in June 2016, countless hours and work have been put in behind the scenes to make the program and brand what they are today. We have helped over 40,000 businesses become more competitive and successful, and there could not be a more meaningful metric as we continue to build healthy and vibrant main streets and communities. As we all know, small businesses are both the heart and economic drivers of our communities.

I could not be prouder of how far the program has come since the night when I drew on that napkin, but I know we still have a long road ahead of us and look forward to continuing our support of small businesses for the next 1,825 days and beyond.”

John Kiru, Founder – Digital Main Street, Executive Director – TABIA


The original napkin, depicting the original idea and visualization for Digital Main Street in 2014


Partnership, Partnership, Partnership

If I could describe the genesis and continued success of Digital Main Street in one word, a lot of potential options come to mind. The one that stands out the most – partnership. Every aspect of the program is rooted in partnerships and continues to be our biggest strength.

  • The City of Toronto for investing time and resources to help build out the platform over the 18-month design period.
  • Our founding corporate partners who believed in our idea and vision and helped us get the program off the ground: Mastercard, Shopify, Google, Rogers, Yellow Pages, and Microsoft, as well as our partners who have joined the network over the last 5 years: Facebook, Square, Intuit QuickBooks Canada, and Lightspeed.
  • Our government partners who have supported our growth: the Ontario Government (Ministry of Agriculture, Food and Rural Affairs and Ministry of Economic Development, Job Creation and Trade), Federal Government (FedDev Ontario) and more helping us expand our reach and help businesses across Ontario.
  • Our regional delivery partners in Ontario who have formed such a strong community of support that has been amazing to be witness to. This includes Municipalities, Small Business Enterprise Centers, Regional Innovation Centers, BIAs, Chambers of Commerce, and more. I would be remised if I also didn’t highlight our regional partners across the Country who have supported us and allowed us to support businesses in communities across Canada from east (Halifax, Cape Breton) to west (Maple Ridge, Calgary, Edmonton, Lloydminster, Medicine Hat and more)


Without everyone of you this would not have been possible – so THANK YOU.



Mayor John Tory kicking off the DMS Launch event, June 2016


Founding DMS partners speaking at the Launch event, June 2016                                                   


Staying true to the mission

Over the last 5 years, the program has changed, grown, adjusted, pivoted and adapted many times but at the root of it all our main focus has not shifted. It has and continues to be the health and viability of main street businesses across Canada (and North America). This unwavering focus has allowed us to grow as a team, introduce new programming and more, all while keeping thefocus solely on the businesses and business owners.

Some quick notes on pivots and adjustments to the program over the last 5 years:

  • In 2017 we doubled down on our Digital Service Squad footprint and increased the size of the team, realizing the direct support to businesses was needed
  • In 2018 we expanded the program from just Toronto to a provincial wide program in Ontario in partnership with the Ontario BIA Association (OBIAA)
    • Introduced multiple new programs and streams of funding for businesses and municipalities
  • In 2018 we launched our fully accessible and free Learning Management system to house our online learning – a first of its kind sweet of online courses available to businesses and business owners whenever, wherever, however fits their schedule and needs
  • In early 2020 we pivoted our Digital Service Squads from in-person to completely virtual to respond to world issues
  • In early 2020 we launched two new programs (ShopHERE powered by Google, and FutureProof) in direct response to the COVID-19 pandemic
    • These were expanded across Ontario with support from the Province and FedDev Ontario, and in collaboration with Communitech, Invest Ottawa and NORCAT
  • In 2021 Digital Main Street won the “Innovation in Community Resiliency Award” at the EDCO conference for our ShopHERE powered by Google program


How have businesses responded?

When the program first launched, Digital Main Street was victim to a very famous cliché. “If it sounds too good to be true, it probably is”. A staple of the program that has and will not change is availability to all businesses. Digital Main Street does not charge businesses a single cent for support or accessing our site and resources, etc. As you can imagine, approaching business owners who are used to being solicited far too many times on a weekly basis with a value proposition of “We are here to provide support, and it is completely free” was met with skepticism from business owners “waiting for the other shoe to drop”, or for a surprise invoice to show up.

To date, the program still faces skepticism at times, but because of our partnerships and delivery structure–hyperlocal engagements are built out regionally across the board and these help break the ice with businesses. Dealing with this initial hurdle prepared the team for any issue moving forward as we essentially had to sell something that was free.

Some business highlights:

  • Have supported over 40,000 businesses to date across Canada
  • Have spent almost 50,000 hours providing direct 1-1 support to businesses, in the form of consultations with our Digital Service Squads, eCommerce Coordinators, and more.
  • Have supported over 17,000 businesses through our ShopHERE program helping businesses become eCommerce enabled
  • Have provided almost $15,000,000 in grant funding to small business owners to invest in Digital Transformation for their business


“ The Transformation Teams Program was helpful in addressing many of our digital marketing initiatives. The program was very beneficial in adding to our online presence. It also opened up more opportunities to market our business for free, without the tremendous costs that would normally come with a digital marketing team. Working with the Transformation Teams is a great opportunity for businesses to expand their reach to potential customers at no cost to them. The Transformation Teams program sets businesses up with all the tools they need to digitally market themselves.”

Anthony Kyriakopoulos President of Buzz Buzz Pizza


“Digital Mainstreet has been extremely knowledgeable and helpful with my Facebook and Google advertising, and made sure those platforms were properly connected to my Shopify store.  They also taught me how to read my Shopify and Google analytics, and were happy to help with any questions I had about my website.  Digital Mainstreet's student helpers – have been very patient, pleasant and a pleasure to work with.”


Caley, owner of Caley-Beth Inc


“Loved the ShopHERE program. Gave us a fighting chance to maneuver in our current environment, where too many small businesses are struggling to survive. Our Coordinator was beyond our expectations. Honestly, she was incredible. So efficient, kind and patient. ALWAYS willing to help with a smile.”


Susan and Drew, owners of Dumpling’s Treats


Investing in our future

Digital Main Street is a business focused program, but also at the root of our mission is Youth Employment and upskilling youth looking to either break into the industry or make a career shift. Since program inception Digital Main Street has been called home by over 1,800 youth across Canada. We have been able to craft top tier training programs and work-integrated-learning opportunities with our partners, all while providing support to businesses!

Digital Main Street has been fortunate to collaborate with partners like Google on their Talent Match program, providing unique access to entry level jobs for Digital Main Street alumnus. The program will continue to focus on it’s role in upskilling youth across the Country and will look to build on existing training and infrastructure with accredited certifications and more!



You are only as good as the support you have around you

I like to think our team at Digital Main Street is a lot like Bradley Cooper in the movie Limitless. At one point in the movie, he is quoted as saying “If I wasn’t moving forward, I felt like I was going to explode”. While this is quite extreme, I think it sums up our teams’ constant desire for improvement and wanting to look for new and innovative ways to bring direct support to small businesses. With passion leading the charge, we are always pushing the envelope and never resting on our laurels. 

Some of these words have been used before when the program won an EDCO award earlier this year , but they remain true and probably more relevant than ever. In my many roles at DMS (now as Managing Lead) I have been blessed to be surrounded by incredible leaders, mentors, team members, and more. Without adding a few more chapters to this post by naming everyone that has influenced Digital Main Street over the last 5 years, it is important that we highlight everyone who has ever spent time with Digital Main Street as an employee in any capacity.

The level of drive, passion and determination shown everyday keeps us motivated and supporting each other as we chase common goals. Whether it was 4 years ago when it was just Lucila Machado and myself at a shared table in the Centre for Social Innovation, or now when we have hundreds of staff across the province and beyond – thank you! The program is not what it is today without every single person who has touched it and had a hand in building it.

Winston Churchill once said “Success is walking from failure to failure with no loss of enthusiasm” – and I cannot think of a better quote to sum up the work our team has done. Not once has the enthusiasm and passion they show wavered.

This has manifested itself in incredible growth for the Digital Main Street brand and program over the last 5 years. Starting out in just Toronto supporting 82 BIAs (at the time), the program is now in 450+ municipalities across Canada, have a presence in the United States, and have engaged stakeholders as far as Australia.


What’s next?

As we look at what the future holds for Digital Main Street one thing is clear, we are going to continue growing our support for small businesses across the country and North America as we build on our position as the preeminent small business digital support program. We approach the future cautiously optimistic that the future of Small Businesses is now more than ever going to rely on Digital Transformation and having an online presence, and we plan on being there every step of the way supporting them.

Digital Main Street has been a labour of love driven by incredible partnerships, leadership, passion, and desire to make small businesses as competitive and resilient as possible. There are a million different pieces that went into making the Digital Main Street puzzle with each being as critical as the last.



-Darryl Julott, Managing Lead

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