Dean Bedwell works with organizations to optimize their Microsoft licensing agreements. He also trains organizations on Microsoft licensing negotiation strategies and tactics.
Before joining Directions on Microsoft, Dean was president of Software Asset Advisors, a software licensing consultancy. Prior to that, Dean spent twelve years at Microsoft managing the Canadian Business Desk where he was responsible for negotiating agreements with Microsoft’s largest enterprise and public sector customers.
Dean received a B.A. in biology from McMaster University.
Latest Content by Dean Bedwell
Video
Updated: December 22, 2025 · by Multiple Authors
Directions Podcast. Season 4. Episode 21. Microsoft Licensing and Negotiation: A Year in Review
Directions on Microsoft’s chief negotiator Dean Bedwell shares licensing and negotiation trends (along with a few tips) with Mary Jo...
Video
Updated: December 17, 2025 · by Multiple Authors
Directions Podcast. Season 4. Episode 20. Moving From EA to MCA? Watch Out for These Gotchas
As Microsoft transitions more customers off Enterprise Agreements and onto MCAs, orgs need to be aware of some potentially costly...
Video
Updated: August 27, 2025 · by Multiple Authors
Directions Podcast. Season 4. Episode 14. Get Ready for Microsoft’s Coming Licensing Changes.
Starting Nov. 1, Microsoft is dropping the programmatic discounts that were baked into its volume-licensing agreements. But price hikes are...
Podcast
August 30, 2023 · by Dean Bedwell
Microsoft EA Negotiation Podcast Series – Negotiation
In this fourth installment of a series covering Microsoft Enterprise Agreements (EAs), Directions on Microsoft's director of advisory services and...
Analyst Report
Updated: May 31, 2023 · by Dean Bedwell
Negotiating a Microsoft EA
In this episode, Mary Jo Foley talks to veteran negotiator Dean Bedwell about Microsoft Enterprise Agreements.