The major partners behind Calgary Small Business Week are doing more than putting their names on an event. They are supporting the entrepreneurs, employers and innovators helping drive the city’s economy forward.
Small businesses may be small by definition, but their collective impact on Calgary is anything but.
More than 63,000 businesses operate in the city, and 95 per cent of Calgary’s business community is made up of small businesses, according to the Calgary Chamber of Commerce. Calgary’s small-business sector contributes to a $129-billion economy, the highest GDP per capita in Canada.
Those numbers help explain why Calgary Small Business Week continues to attract support from organizations that recognize the importance of the city’s entrepreneurial community.
Through the Calgary Chamber, Small Business Week will feature a variety of events from Oct. 19 to 23, bringing the business community together to connect, learn and celebrate entrepreneurship. The festivities culminate in the Calgary Small Business Awards Gala on Oct. 23 at the Hyatt Regency Calgary.
This year, Alberta Blue Cross serves as title sponsor, with Always Beyond, Chambers Plan Employee Benefits and Mastercard among the supporting sponsors.
Alberta Blue Cross: Supporting Alberta Communities
As title sponsor of Calgary Small Business Week, Alberta Blue Cross brings a long history of investing in communities across the province.
Through the ABC Benefits Corporation Foundation, established in 1998 to celebrate Alberta Blue Cross’s 50th anniversary, the organization supports community investments focused on wellness. Its programs include Built Together, which funds infrastructure projects that encourage active living and community connection across Alberta.
That commitment provides a fitting backdrop to its role as title sponsor of a week recognizing Calgary’s entrepreneurs and the businesses they build.
Always Beyond: From Award Winner to Sponsor
For Calgary-based IT company Always Beyond, supporting Small Business Week is personal.
“Small businesses are the backbone of Calgary’s economy, and they’re the clients we serve every day,” says Sean Freeman, CEO of Always Beyond. “Supporting Small Business Week is a natural extension of that. We get to celebrate the people who take real risks to build something, and as a small business ourselves, we know exactly how much grit that takes.”
The company returns to Small Business Week from a distinctly different position this year. In 2025, Always Beyond received the Calgary Chamber’s Emerging Growth Award.
Freeman says the recognition had an impact both inside and outside the company.
“For our team, the award was validation that the work they put in every day is making a real difference for clients,” he says. “Externally, it raised our visibility with small and medium-sized businesses across the region.”
Returning as a sponsor, he says, feels like the right way to close the loop, moving from being recognized to helping shine a light on the next group of growing companies.
It comes during a significant year for Always Beyond. Freeman says the company completed its SOC 2 Type 2 certification, launched a SaaS and AI Governance service and is moving into a new Calgary office this fall. The company also continues to grow at more than 40 per cent annually.
That growth is happening as small businesses face an increasingly complex technology environment.
“The most common thing we hear is ‘we’re too small to be a target,’ and unfortunately that’s no longer true,” Freeman says.
Attackers are increasingly automating their efforts, meaning smaller companies can face many of the same threats as larger organizations. Freeman says business owners are also feeling pressure from cyber insurance requirements and the rapid adoption of artificial intelligence in the workplace.
Cloud technology and remote work have further changed how businesses need to think about security.
“Ten years ago, you could protect a business by protecting the office,” Freeman says. “Now your data lives in dozens of cloud apps, your team works from home, hotels and coffee shops, and your identity is the new front door.”
Always Beyond describes its approach as “human-first” IT, acting like a client’s IT department rather than simply responding when something breaks. For businesses without internal IT staff, that can mean providing oversight across security, strategy, support and planning.
Freeman encourages entrepreneurs to treat technology as part of their overall business strategy rather than a series of reactive purchases.
“Treat technology as an investment with a plan, not a series of emergency purchases,” he says. “The companies that grow smoothly are the ones where IT is part of the strategy conversation, not an afterthought.”
Chambers Plan: Helping Small Employers Compete
For Chambers Plan Employee Benefits, small business is not simply a market segment. It is the reason the organization exists.
In responses provided collectively by Chambers Plan Advisors, the organization emphasizes that its focus has always been on serving Canadian small businesses.
“Small business is at the heart of everything we do. Chambers Plan was built specifically for Canadian small businesses and exists to help business owners take care of their people, navigate challenges with confidence and focus on growing their business.”
That makes supporting Calgary Small Business Week a natural fit.
“It’s an opportunity to celebrate the entrepreneurs and business owners who contribute so much to Calgary’s economy and community, while reinforcing that they don’t have to navigate the challenges of running a business alone.”
Through the Calgary Chamber, local Chambers Plan Advisors and the broader Chamber network, business owners can access resources and expertise developed with the realities of small business in mind.
One area where that support can be particularly important is employee benefits.
Small businesses often compete for employees against much larger organizations, but may not have the same resources, purchasing power or dedicated human resources teams.
“For a small business owner, every employee matters,” the advisors note. “When you’re a team of five or 10 people, losing one great employee or having someone away for an extended period can have a significant impact on the entire business.”
Benefits can play an important role for smaller employers, but navigating the market can also be challenging. Chambers Plan Advisors point to the complexity of the group benefits market as one of the difficulties business owners face.
“The group benefits market can be complex and crowded, making it difficult to know which plan is the right fit.”
Through Chambers Plan’s partnership with the Calgary Chamber, businesses have access to local advisors who understand the market and can help employers navigate their options.
For owners already balancing operations, finances, growth and people management, that expertise can help make benefits decisions more manageable.
As the advisors put it, “We are proud to be part of that network and, ultimately, to be in service to small business.”
Mastercard: Supporting Small-Business Resilience
Supporting sponsor Mastercard offers programs and resources aimed at helping Canadian small businesses navigate an increasingly digital economy.
Its Small Business Navigator, launched in Canada in 2025, brings together resources to help small-business owners simplify operations, control costs and improve efficiency, including economic insights, cost-saving opportunities and cybersecurity resources.
Mastercard also provides cybersecurity education and tools through its Canadian Trust Centre.
A Shared Investment in Calgary
Technology is changing quickly, cybersecurity risks continue to evolve and attracting and retaining employees remains competitive. At the same time, small-business owners must manage costs, customers, people and growth.
Calgary Small Business Week provides an opportunity to recognize what entrepreneurs continue to accomplish despite those pressures.
Behind the statistics are thousands of business owners taking risks, creating jobs, adapting to change and contributing to their communities.
The organizations supporting Small Business Week bring different expertise to that ecosystem, from health and community wellbeing to technology, employee benefits and financial tools. Their involvement points to a common recognition of the role small businesses play in Calgary.
For Freeman, that contribution comes back to the people willing to build something of their own.
“Small businesses are the backbone of Calgary’s economy,” he says.
And in a city where 95 per cent of businesses are small, supporting their success is also an investment in Calgary’s future.