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Skyline is a growth-oriented firm that serves as an investor and advisor for small to medium sized private enterprises in the Legal Services and e-Discovery space to develop capabilities and infrastructure to assist organizations with scaling operations effectively.

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We are looking to invest in businesses that exhibit the traits below.  Of course, every business is different, and we are always willing to have a conversation if you are not sure your business fits all of the below criteria.


  • Legal Services

  • Business Services

  • IT Services 

  • Software


  • Strong team and growth culture

  • Located in the United States or Canada

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Prior to co-founding Skyline, Freddie was an operating partner primarily across the manufacturing space. He successfully turned around a distressed chemical company resulting in significant positive cash flows in two years. He also led the sale of Segway to a strategic acquirer. His experience as an operating partner for the firm focused on leading teams and overseeing internal operations for the portfolio companies.

Before SSI, Freddie co-founded Generis Group - a business conference organizer that grew to become the 11th fastest growing startup in Canada in 2017. He started his career at CPPIB where he completed $4 billion in infrastructure transactions and $200 million in private debt investments. 

Freddie holds a B. Commerce degree from the Smith School of Business at Queen’s University, where he graduated with distinction for academic excellence.




Prior to co-founding Skyline, Dara was the SVP of Operations at Auxly Cannabis Group. At Auxly, Dara stood up the supply chain, product development, partnerships, procurement and planning functions, growing the company from 20 people to over 350 people in two years.


Before Auxly, Dara was an Associate at Oliver Wyman advising Fortune 500 clients on strategy, operations and digital transformations.  Prior to that he was a Senior Manager at Shoppers Drug Mart within the Analytics practice where he led several large transformations resulting in over $75M of gross margin expansion. Dara began his career at Anheuser-Busch InBev as part of the Global Management Trainee program, exposing him to a wide variety of business problems across functions early in his career. 

Dara holds an MBA from the Richard Ivey School of Business, where he was awarded the Ivey Entrepreneurship Award.  Dara also holds a BA (Hons) in Economics from McMaster University where he graduated summa cum laude

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555 Richmond Street West, Suite 1010, Toronto, Canada

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