Shaping future leaders while strengthening local businesses: The lasting impact of the Digital Service Squad Program

For the last 8 years, the Digital Service Squad Program (DSS), run by Digital Main Street (DMS) a part of the Toronto Association of Business Improvement Areas (TABIA), has become an essential program for small locally-owned businesses.

For most, the DSS was best known for its role in helping brick-and-mortar businesses with their digital transformation, helping them grow online and reach more customers. But the program’s influence ran far beyond the storefronts that were supported.  For most, the DSS was best known for its role in helping brick-and-mortar businesses with their digital transformation, helping them grow online and reach more customers. But the program’s influence ran far beyond the storefronts that were supported.  

The DSS team consisted of passionate youth, recent grads, and others with expertise in technology and digital marketing, known as Digital Service Squad members. These DSS teams provided free, personalized, one-on-one support to help eligible small businesses get started online and improve their digital presence.  

For those who worked within the program as DSS members—like Thomas Strongman, Dylan Tamlin, and Khushi Patel—the program was a springboard for personal and professional development. When young professionals joined the DSS they weren’t just signing up to help small businesses thrive online—they were stepping into roles that built leadership, resilience, and local community. Thomas, Dylan and Khushi’s journeys highlight how the DSS program shaped future leaders while strengthening local businesses. 

Thomas’s Story 

When Thomas Strongman graduated from Conestoga College’s broadcast video production program, the world was in the throes of a global pandemic. Faced with an uncertain future, Thomas turned to his video production skills and started working independently. Despite finding some success, he longed for a more traditional work path.   

While seeking support for his business, Thomas stumbled upon resources from his local enterprise centre. A short while later, he came across a job posting for a role with the Small Business Enterprise Centre in Kitchener-Waterloo, as part of their Digital Service Squad.  

“It was interesting,” Thomas reflects, “because I’d already looked into the program resources on my own. Then it came full circle, I now had the opportunity to assist with similar programs.”

Thomas was hired as a DSS and together with five others worked to support small and medium businesses across the Waterloo region with their digital transformation. His photography and video expertise proved valuable, but it was the connections he forged with business owners that truly set him apart. He became a bridge between the community and the tools they needed to thrive online. But working as a DSS wasn’t just beneficial to the businesses support, but Thomas as well.  

“Being a DSS was highly valuable (and) a massive learning opportunity”, he shares. “The opportunity for youth to become more involved in a professional ecosystem was really good for not just myself, but all members of the DSS.”

The connections and skills Thomas gained helped him land a new role with the City of Cambridge’s Economic Development Department, where he continues to apply the expertise, he first cultivated through his time on the Digital Service Squad. 

“The networking I did as a DSS gave me the platform to be considered for an economic development role.”

Dylan's Story 

Like Thomas, Dylan Tamlin also discovered his passion for supporting small businesses early in his career. While earning his degree from Trent University, he gained experience in digital marketing at the Bobcaygeon Chamber of Commerce, finding a deep satisfaction in helping local communities grow. 

“I really like to help out the communities that I’m living in, and the main way (I can do that) is working with small businesses”, Dylan shares.  

When a short-term DSS opportunity arose in Lindsay in 2021, Dylan jumped at the chance to contribute. During his time as a DSS, Dylan worked to help small businesses in Kawartha Lakes apply for digital transformation grants, and despite the contract's brevity, he found himself making a meaningful impact. 

After finishing his degree, Dylan relocated to St. Catharine's, where he once again joined the DSS. As a DSS in St. Catharine's, Dylan was able to assist more than 120 business owners with their expansion online and improving their marketing. He also worked alongside the other St Catharine's DSS members to secure north of a quarter million dollars in grant funds for small businesses in the area.  

“It was amazing to see the impact I could have being one person”, Dylan reflects. “I found that I really loved the environment, and it was exactly what I wanted to do… The collaboration that can be found by (connecting) youth with new ideas to older brick and mortar stores is amazing to see.” 

After a year, Dylan applied for a full-time position in the business enterprise centre with the City of St. Catharine’s, which is now his current role.  

“From all the skills I gained as a DSS dealing with clients and providing 1-1 support diving into their problems, I was a natural fit for the role”, he shares proudly.  “Those soft skills aren’t always taught. You have to learn them yourself, and that is something (working as a DSS) really allowed (me to do).” 

Khushi's Story 

For Khushi Patel, supporting small businesses was part of her DNA, thanks to her family’s long history of entrepreneurship. After working as an IT developer in India, Khushi came to Canada as an international student in 2018. A few years later, she was ready to start her co-op internship when the pandemic struck. Like so many others, she found herself struggling to secure work.   

She heard about an opportunity through Digital Main Street – Future Proof program and applied to be a UX/UI designer. A few days later, she accepted the position, which led to a long history of working with DMS.  

 “I first (started) working with DMS on the Future Proof Program as a UX UI Designer, then worked for the ShopHERE program as an E-commerce Coordinator, then became a Digital Service Squad member with the City of Kitchener.” 

As a DSS in Kitchener, Khushi was tapped on for her extensive UX/UI experience, which businesses are often looking for support with but don’t have the budget to do so.  

“My background gave me a platform to utilize that skill set. There's a lot of small businesses that need that support. It was a great”, she says. “DMS gave me the strength to work directly with small businesses in a new world and new environment”.  

One experience particularly stands out to her: helping a recently retired entrepreneur navigate the digital world for the first time. Through Khushi’s patient guidance, the business owner now confidently manages her own website and digital marketing tools.   

“It was a great experience to work with her. She got emotional and she is still in touch”, Khushi shares. “Thats an achievement and a fulfillment…I (felt) so proud that I could see the tangible results.” 

Working as a DSS gave Khushi important, employable experience too. After her time as a DSS, Khushi applied for and was hired to be an Entrepreneurship and Technology advisor with the Waterloo Region Small Business Centre. She is the youngest advisor in the position and brings her unique passion and experience to the role.  

“DMS gave me the experience (and) lead to this big role…DMS brought this all. They gave me the opportunity.”  

The stories of Thomas, Dylan, and Khushi highlight the powerful influence the DSS program has had on both small businesses and the individuals who work with them. Creating connections between young professionals and the small businesses they worked with has and will continue to have a lasting, strong impact on the resilience and economic development of the businesses and the local community.  Thomas, Dylan and Khushi’s experiences illustrate how hands-on support can spark professional growth, deepen community ties, and foster a shared commitment to local, small business success. 

These stories would not be possible without the support of our partners, with a special thank you to FedDev Ontario, the Province of Ontario (MEDJCT), the Government of Alberta (JET), and the City of Toronto for their ongoing support, as well as OBIAA, Business Link, and everyone else we have worked with to make our program a success.