William Rosenberg Foundation Leadership Award Winner: Dan Monaghan, CFE

February 2025
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Named in honor of the man whose vision and leadership led to the creation of the IFA Foundation, the William Rosenberg Leadership Award is presented each year to an individual with outstanding contributions and leadership in advancing the mission of the IFA Foundation. The 2024 recipient of this award is Dan Monaghan, CFE, the managing partner of Clear Summit Group (CSG).

While most kids were dreaming about sports and summer fun, young Dan Monaghan had his nose buried in Entrepreneur magazine, fantasizing about owning a Dairy Queen franchise. This early fascination with franchising would later blossom into a remarkable entrepreneurial journey that would help shape the digital marketing landscape worldwide.

After cutting his teeth with a Dickie Dee ice cream franchise that helped fund his education at Wilfrid Laurier University, Monaghan’s true entrepreneurial story began in 1995. At age 27, together with his younger brother Paul, he founded WSI (We Simplify the Internet) two years before Google existed. With just $50,000 in capital from friends and family, they launched what would become the world’s largest digital agency network.

The early years of WSI were marked by pioneering spirit and missionary zeal. In an era when fax numbers were the standard of business communication, Monaghan and his team embarked on an ambitious global journey to educate business leaders about the coming information age. They would purchase round-the-world tickets that allowed unlimited stops as long as they kept traveling east, enabling them to conduct seminars in cities across the globe for skeptical business leaders about a revolutionary technology called the Internet. “I would explain that in the years to come, everyone would have an email address on their business card the way they have a fax number today,” Monaghan recalls. “Most would stare at me with either confusion or disbelief.” Those blank stares would eventually turn to understanding as WSI’s vision proved prescient. Three decades later, WSI has developed over 500,000 sites and solutions for companies worldwide.

Building on this foundation of digital innovation, Monaghan founded Clear Summit Group (CSG), a franchise accelerator that manages seven brands across 80 countries with over 1,500 franchises. His portfolio includes numerous transformative success stories, with several brands growing from small emerging franchises to hundreds of locations across multiple countries under his leadership.

What sets Monaghan apart is his commitment to meaningful impact through business. All CSG ventures are service-based and designed to make a difference in their communities. Monaghan’s investment philosophy centers on long-term collaboration and mutual growth. “We are bringing capital to the table, but it is more about building a collaboration among partners,” he explains. “We are learning as much from our CEO peers as they are learning from us.”

His influence extends beyond his own business ventures, serving as Past Chair of the IFA’s Foundation and currently sitting on the IFA Board of Directors, while actively supporting Canada’s growing role as a franchising hub. He is also the founder of the Make Child Poverty History program, a humanitarian initiative developed in conjunction with World Vision. Monaghan is particularly passionate about Canada’s potential as a franchise incubator, especially in harnessing technology for business innovation.

Through three decades of technological revolution, Monaghan’s ability to anticipate and harness change, while nurturing exceptional teams and maintaining a relentless focus on customer success, has created a legacy of innovation that continues to evolve and inspire the next generation of entrepreneurs.

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