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We’re the Microsoft Experts Every CIO Wants

Our Microsoft experts are the type of people every CIO wants to hire but usually can’t find or afford. Each brings an average of 25+ years of industry experience, including former Fortune 500 CIOs, former Microsoft product engineers, and a former Microsoft CTO. Our experts also include former executives from the Microsoft Business Desk, the highest level of the Microsoft licensing organization.

Their mission is to make the objective facts and deep insights you need easily available and digestible so you can make smarter, faster decisions about Microsoft.

How We Can Help

Founders

Jeff Parker

Analyst

Jeff Parker oversees Directions on Microsoft’s publishing and training businesses. He also advises clients on Microsoft partnering strategies. Prior to…more

Rob Horwitz

Analyst

Rob Horwitz analyzes and writes about Microsoft licensing programs and product licensing rules. He also trains organizations on best Microsoft…more

Former Microsoft Executives

Dean Bedwell

Licensing Expert & Negotiator

Dean Bedwell works with organizations to optimize their Microsoft licensing agreements. He also trains organizations on Microsoft licensing negotiation strategies…more

Barry Briggs

Analyst

Before joining Directions on Microsoft in 2020, Barry worked at Microsoft for 12 years in a variety of roles, including…more

Greg DeMichillie

Analyst

Greg brings with him over two decades of engineering, product and GTM experience. He has held leadership positions at premier…more

Microsoft Insider Experience in Technology

Wes Miller

Analyst

Wes Miller analyzes and writes about Microsoft’s security, identity management, and systems management technologies. Before joining Directions on Microsoft, Wes…more

Rob Sanfilippo

Analyst

Before joining Directions on Microsoft, Rob worked at Microsoft for 14 years where he designed technologies for Microsoft products and…more

Michael Cherry

Analyst

Michael analyzed and wrote about Microsoft’s operating systems, including the Windows client OS, as well as compliance and governance. Michael…more

David Berry

Analyst

David specializes in SharePoint and Microsoft 365. He spent 25 years as a solution architect and advisor consulting with Fortune…more

Microsoft Insider Experience in Licensing, Negotiation and Account Management

Steven Kelley

Negotiation & Audit

Steve Kelley works with organizations to optimize their Microsoft licensing agreements and protect them from future licensing liabilities. Before joining Directions…more

Kevin Glunt

Negotiation & Audit

Before joining Directions on Microsoft, Kevin spent eleven years at Microsoft in financial management, including five years as the senior…more

Scott Campos

Negotiation & Audit

Prior to joining Directions on Microsoft, Scott was a Microsoft licensing consultant at IDC and Software Licensing Advisors. Before that,…more

Joshua Osborne

Negotiation & Audit

Joshua Osborne helps organizations to optimize their Microsoft licensing negotiation outcomes. He also works with companies to self-audit their Microsoft…more

Larry Fletcher

Negotiation & Audit

Larry is a former Senior Licensing Executive at Microsoft with over 15 years experience negotiating complex deals within both the…more

Respected Independent Voices

Mary Jo Foley

Analyst

Mary Jo Foley is the Editor in Chief at Directions on Microsoft. Before joining Directions, Mary Jo has worked as…more

Andrew Snodgrass

Analyst

Andrew analyzes and writes about Microsoft’s data management, business intelligence, and machine learning solutions, as well as aspects of licensing…more

Rob Helm

Analyst

As managing vice president, Rob Helm covers Microsoft collaboration and content management. His 25-plus years of experience analyzing Microsoft’s technology…more

Jim Gaynor

Analyst

Jim leads the Directions on Microsoft editorial team and has been writing about technology since the early 1990s. Most recently…more

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