Alumni Executive

List of 9 members.

• 

  Mr. Jake Cassaday 06

  Bio +

  Jake Cassaday serves as CEO of ALT Sports Data, where he leads the development of an operating system that turns emerging and alternative sports event data into scalable global products.

  His career spans executive leadership, venture capital, and operations at the intersection of sports, media, technology, and gaming. Prior to ALT Sports Data, Jake spent seven years investing in early-stage technology businesses at Relay Ventures. He also helped launch sports media platform Playmaker Capital as Chief Operating Officer. Following Playmaker's acquisition by Better Collective, he served as CEO Canada and SVP of Strategy & M&A.

  Jake holds a BA from McGill University and an MBA from the Rotman School of Management. A Crescent alumnus from the Class of 2006, he currently co-chairs Crescent's Alumni Executive Committee. He lives in Toronto with his wife and three children (Max, Robbie, and Madeline).
• 

  Mr. Patrick Osler 96

  Bio +

  Patrick Osler is Managing Principal, Senior Portfolio Manager, and Head of Private Wealth at Westcourt Capital, a multi-family office serving ultra-high-net-worth families.

  He leads the Private Wealth team, overseeing client servicing, portfolio construction, strategic growth, and serving on the Senior Leadership Team and Investment Committee. Before joining Westcourt, Patrick spent over two decades at a leading boutique Canadian asset manager in progressively senior roles, ultimately serving as head of the wealth management business, where he directed end-to-end client experience and independent investment solutions.

  Patrick earned his undergraduate degree from the Williams School of Business at Bishop’s University and holds the Chartered Financial Analyst (CFA) designation. A 1996 Crescent graduate, he co-chairs the Alumni Executive Committee. He resides in Toronto with his wife and two sons, Burke ('31) and Freddie ('33), who both attend Crescent.
• 

  Mr. Jeff Ballard 08

  Bio +

  Jeffrey Ballard is Assistant Vice President, Executive Lines at Banyan Risk Ltd., a start-up MGA he joined in 2023. With over a decade of experience in the insurance sector, he focuses on underwriting executive and financial lines risk.

  Jeffrey began his career in 2013 with a leading global insurer before moving into his current position. He holds an HBA from the Ivey Business School at Western University and actively mentors emerging industry talent as a designated mentor with the Professional Liability Underwriting Society (PLUS).

  Jeffrey started his journey at Crescent in Grade 3 and graduated in 2008. Outside of his professional life, he enjoys traveling, spending time with his family, and avidly supporting the Toronto Maple Leafs.
• 

  Dr. Karn Dev 98

  Bio +

  Karn Dev is the owner and practicing dentist at Dev Dental, a network of dental clinics operating across the Greater Toronto Area and surrounding communities.

  After graduating from Crescent, Karn earned his undergraduate degree in Human Biology from the University of Toronto and his Doctor of Dental Medicine from Boston University. He completed advanced postgraduate training in New York City, serving as Chief Resident at Montefiore Medical Center, before practicing in the New York area and eventually returning to Toronto.

  A Crescent lifer who attended from Grade 4 through graduation, Karn served as House Captain and Prefect. Grateful for the mentorship and community Crescent provided, he looks forward to giving back through the Alumni Executive Committee.
• 

  Mr. Cole Halbert 14

  Bio +

  Cole Halbert is a corporate lawyer specializing in mergers and acquisitions, private equity, private investment funds, and corporate/commercial matters across domestic, cross-border, and international transactions.

  Cole previously practiced at the national law firm Fasken Martineau DuMoulin LLP and completed a secondment with the Canadian Olympic Committee. He holds a JD from Western University, a BA (magna cum laude) from Duke University, and completed the Business Bridge program at Dartmouth College’s Tuck School of Business.

  An active alumnus, Cole serves as the Class of 2014 Representative and leads his year’s bursary endowment fund. In his spare time, he enjoys playing tennis, skiing, watching Duke basketball, listening to TED Talks, and traveling to over 50 countries.
• 

  Mr. Christopher Hatsios 12

• 

  William C Krstajic 20

  Bio +

  Will Krstajic is an Associate at Thomvest, assisting in investments across the private market landscape through both fund and direct positions. Thomvest is the single-family office of Peter Thomson, a member of the broader Thomson family.  

  He graduated with a Bachelor of Commerce (Hons.), specializing in finance, from the Smith School of Business at Queen’s University in 2024. Will is an alumnus having graduated Crescent in 2020. He currently lives in Toronto.
• 

  Mr. Ryan Nelson 05

  Bio +

  Ryan Nelson is a real estate investment and development professional at The Pearl Group, where he focuses on acquisitions, development strategy, and expanding the firm's platform across North America.

  Throughout his career, Ryan has worked across investment, development, asset management, and advisory roles, focusing on complex urban real estate opportunities and community-focused city-building.

  Ryan joined Crescent in Grade 9 and graduated in 2005. He remains closely connected with his classmates, participating in an annual canoe trip now in its 20th year. He lives in Toronto with his wife, Fabienne, and their three sons (Henry, Tristan, and Oliver), and enjoys golf, fitness, reading, and coaching youth sports.
• 

  Mr. Benjamin Wong 00

  Bio +

  Ben Wong is an entrepreneur and real estate executive serving as the Founder of Skybourne Developments and President of Living Properties and KW Living Realty.

  Ben began his career as a real estate lawyer before transitioning into property management, land development, and construction. Today, he leads and operates multiple real estate and development businesses across the Greater Toronto Area.

  A proud 2000 graduate of Crescent School, Ben is grateful for the lasting impact of his Crescent education. He serves on the Alumni Executive Committee to support and strengthen the broader alumni community. Ben is the proud parent of three boys, Callum, Hunter, and Lincoln ‘31.