As President and CEO, Leigh is responsible for Osprey’s acquisition strategy, the growth of its organic businesses and the development of Osprey’s employees, customers, and partners.
Leigh previously held roles as Chief Revenue Officer (CRO) of Aptum Technologies Inc., a $100M global MSP based in Toronto, Canada. At Aptum, Leigh led Sales, Presales Engineering, Professional Services, Demand Generation Marketing, Customer Support and Revenue Operations globally. Prior to Aptum, Leigh spent over 10 years at SunGard Availability Services in a variety of progressive leadership roles that included Vice President of Sales Northeast US and Vice President Strategic Sales. Leigh holds a Bachelor of Business Administration from Goodman School of Business (Brock University). He has also studied at Schulich School of Business (York University), Sheridan College, and Smith School of Business (Queens University).
Beyond his academic and professional achievements, Leigh has been married for over 15 years and has two sons. He is an active volunteer, coach, and trainer in the OMHA youth hockey program and is also a volunteer with the Halton United Way, which is a not-for-profit charity focused on giving back to the community and supporting local families in times of need.
As Vice President of Pre-Sales Engineering, Grant is responsible for the technology solutions and design of Osprey’s customers, partners and affiliates technology infrastructure across hybrid, public and private environments.
Grant previously held roles as Global Director of Advisory & Consultancy and Director of Pre-Sales Engineering at Aptum Technologies Inc. Prior to Aptum, Grant spent 10 years as a Senior Solution Architect with SunGard Availability Services supporting the digital transformation for Fortune 500 Enterprises, public sector and small-medium businesses. Grant started his career in network security and software development providing enterprise remote management solutions for the Enterprise market and contributed to the successful registration of 3 patents for enterprise network security software.
Grant has successfully achieved industry leading certifications in AWS, VMware, EMC, IBM and numerous backup & recovery platforms. He also studied at George Brown College for web and graphic design certificates.
Outside of his professional experience, Grant is an avid nature lover spending time supporting local farm communities in tree planting, sustainable farm technology including solar and irrigations systems and can often be found fishing or boating on Ontario lakes and rivers.
Jeff is a special advisor to Osprey. Jeff has been involved in IT Services for over 20 years. Jeff is currently the President of ClearIT, operating out of North Carolina and servicing customers throughout the USA. ClearIT’s main focus is to deliver IT Consulting through using best of breed technology and providers.
Jeff previously held roles as VP of Sales (Southeast Region) at TierPoint based in Charlotte, North Carolina as well as VP of Sales for SunGard Availability Services in the Midwest (based in Chicago). Jeff has been successful growing sales regions in both Canadian markets as well as US markets. During his time based in North Carolina, Jeff was an active member of the North Carolina Technology Association. Jeff graduated with a Bachelor of Business Administration from Brock University.
As Revenue Operations Manager, Kyle oversees Osprey's financial strategy, drives the growth of its core operations, and ensures the success and development of Osprey's customers, and partners.
Kyle has built a solid foundation in sales and business development, starting in the sales organization with Equinix, where he gained hands-on experience in the colocation sector. Kyle then advanced to an Inside Sales role at Digital Realty, focusing on generating pipeline and relationship management. Most recently, Kyle served as an Account Executive at Fulcrum IT Partners, managing client accounts and driving business growth through strategic engagement and support. Kyle holds a Bachelor’s degree in Economics from the Lazaridis School of Business and Economics at Wilfrid Laurier University. Outside of his professional experience, Kyle grew up playing competitive hockey and has a deep passion for the sport. He has also been involved in community service, volunteering as a counselor at Kids4Kids leadership camp, and the Oakville foodbank. Today, Kyle continues to channel his love for hockey by playing regularly, and he also enjoys long-distance running in his free time.
As Head of M&A, Matthew oversees Osprey’s acquisition strategy, guiding the identification, evaluation, and execution of strategic growth opportunities. He is responsible for managing due diligence, transaction execution, and post-acquisition integration to ensure long-term growth for Osprey, its customers, and partners.
Matthew has a strong background in capital markets, deal structuring, and strategic acquisitions. After graduating from Western University in 2021, Matthew co-founded a Capital Pool Company that successfully completed a Qualifying Transaction, leading to its public listing on the TSX Venture Exchange (TSXV). Through this venture, he gained extensive experience in capital raising, financial due diligence, and the acquisition process—skills that he now applies to identifying and executing strategic M&A opportunities for Osprey.Prior to joining Osprey, Matthew worked as an Account Executive at Fulcrum IT Partners, where he focused on business development and client relationship management.Outside of his professional career, Matthew is actively involved in charitable organizations, supporting the Oakville, Milton, and Phoenix Humane Societies. He is also an avid golfer and aviation enthusiast – A licensed pilot with over 100 hours of flight experience.
