Our Leadership

Leigh Plumley

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.

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Grant Duxbury

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 Waide

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.

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