Digital Main Street Lab

Working with his team, Chris worked to develop the Digital Main Street Lab - an testing ground for new retail technologies in Toronto.

Leveraging Toronto's diverse and vibrant main streets, the Digital Main Street Lab connects retail technology companies with local business improvement areas allowing them to pilot new technologies.

The purpose of the Lab is to assist Toronto's main street businesses in adopting new technologies, while also encouraging the growth of Toronto's retail technology sector.

StartUp HERE Toronto Cafe

Looking to connect Toronto's entrepreneurs with networks of mentors and advisors, Chris led an initiative to develop a mentoring platform in partnership with other business support organizations in Toronto.

The StartUp HERE Toronto Cafe facilitates connections between entrepreneurs and mentors through online engagements, in-person coffee meetups and monthly group mentoring events.

The StartUp HERE Toronto Cafe has a membership of over 2,000 entrepreneurs and mentors - and grows every week - that results in over 500 coffee meetups between entrepreneurs and advisers each month.

Digital Main Street

Recognizing the growing need to support main street businesses in adapting to the digital economy, Chris led the creation of Digital Main Street—a flagship program designed to accelerate technology adoption and digital literacy across local business communities.

The program combined hands-on support with accessible tools and training, offering:

• A web-based platform to assess digital readiness and provide customized recommendations;

• A Digital Service Squad that worked directly with entrepreneurs to implement foundational technologies like Google Business Profiles;

• A suite of training resources to build digital skills and confidence among small business owners.

Backed by public and private sector partners—including Yellow Pages, Mastercard, Rogers, Google, Shopify, Microsoft, and Canada Post—Digital Main Street scaled rapidly and became a nationally recognized model for supporting digital transformation on main streets.

Digital Main Street was funded by a number of key partners, including Yellow Pages, Mastercard, Rogers, Google, Shopify, Microsoft and Canada Post.

StartUp HERE Toronto

Bringing together key stakeholders from Toronto's innovation community, Chris led the development of the StartUp HERE Toronto brand and web platform as way to better tell the story of Toronto's innovation community.

To strengthen Toronto’s position as a global innovation hub, Chris led the development of StartUp HERE Toronto—a place-branding initiative and digital platform designed to elevate the city’s entrepreneurship story and connect innovators to the resources they need to grow.

Built in collaboration with leading ecosystem partners like MaRS and the DMZ, the platform served as a central hub for Toronto’s innovation community—curating news, events, and success stories while providing a searchable directory of business supports including incubators, accelerators, and co-working spaces.

In addition to aggregating resources, StartUp HERE Toronto produced original editorial content profiling local entrepreneurs and showcasing why Toronto is one of the world’s best places to start and scale a business.

Small Business Taxation - Discussion Paper

Following the Deputy Mayor’s Roundtable on Small Business, Chris led the City’s Small Business Council Advisory Body in the development of a discussion paper examining the property tax challenges facing main street entrepreneurs across Toronto.

The paper identified three core taxation issues disproportionately affecting small business owners and illustrated their real-world impacts through profiles of local operators. By grounding the policy analysis in lived experience, the paper helped humanize the financial pressures reshaping Toronto’s commercial main streets.

This work informed ongoing municipal discussions about equitable taxation and reinforced the need for tailored policy tools to support small business sustainability.

To view the discussion paper visit here.