Webinar
Microsoft Licensing in Transition
Implications for Cost, Contracts and Renewals
Ideal for: Procurement leaders and Microsoft category owners, particularly in large or enterprise organisations facing direct Microsoft engagement
When: Thursday 12 February 2026 at 2pm GMT
Microsoft’s commercial model is entering one of its most unsettled periods in decades.
- Volume discount bands have been removed.
- Pricing is fragmenting by product, component and region.
- Some costs are rising sharply, others are coming down.
- Enterprise Agreements are evolving and for some organisations, disappearing altogether.
For large organisations, particularly those moved into direct engagement models, traditional negotiation levers are disappearing, while cost and complexity continue to rise, resulting in:
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Reduced discount flexibility
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AI-driven licensing expansion
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Renewals with fewer commercial safeguards
As organisations face renewals, many are struggling to answer the only questions that really matter:
What are we paying today, and what does Microsoft expect us to pay next time?
In this webinar, Gareth Redshaw draws on over 20 years of Microsoft licensing experience to cut through the noise and explain what’s really going on behind the changes and why they represent one of the most significant shifts in Microsoft’s commercial strategy in a generation.
This session will explore:
- What’s driving Microsoft’s latest pricing adjustments and programmatic discount removals
- How product-level price increases, regional changes and component pricing are reshaping budgets
- What Microsoft’s evolving go-to-market strategy tells us about future negotiation leverage
- The impact of the direct model has on large enterprises
- Why these changes reflect Microsoft’s growing confidence and how they increase customer lock-in
- What organisations should be doing now to prepare for 2026 renewals and beyond
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Meet your guru
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Gareth Redshaw
Senior Director of Microsoft Optimization and Negotiation consulting at Livingstone
Gareth has been involved IT commercial negotiations for over 20 years and has pivoted from vendor-specific sales roles to developing and executing negotiations for some of the world’s most recognisable brands covering global banking, retailors, technology giants, manufacturers, energy and large public sector departments amongst others.
Follow Gareth on LinkedIn
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