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Microsoft · Case Study · Chicago IT Services

How a Chicago IT services firm saved 3.8 million dollars on the Microsoft EA renewal.

Microsoft opened at fifteen million dollars a year. A mixed E3 and E5 estate, a staged Copilot curve and an honest Azure forecast closed it at twelve point seven.

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Industry Recognized
500+ Enterprise Clients
$2B+ Under Advisory
11 Vendor Practices
100% Buyer Side Independent
Customer
Chicago IT Services Firm
Anonymised. Mid market enterprise scale.
EA Spend
8,000 user EA
Three year EA across M365, Azure and Copilot.
Engagement
16 weeks
Scoping, negotiation, contract finalisation.
Outcome
$3.8M saved
Across the three year EA term.

A Chicago based IT services firm came up on an eight thousand user Microsoft Enterprise Agreement renewal. Microsoft is embedded in how the business runs, spanning Microsoft 365, Azure, Copilot, Dynamics 365, Power Platform and GitHub.

The prior run rate sat near 12 million dollars a year. Microsoft opened the renewal at 15 million. The agreement closed at 12.7 million a year, roughly 15 percent below the opening position and 3.8 million dollars saved across the term.

This is the full engagement, including the analysis that set the counter and the eleven moves that held it. For the wider practice, see the Microsoft advisory practice, the EA 2026 guide, the EA negotiation strategies, and the Microsoft Copilot licensing guide.

Headline numbers

LineMicrosoft proposalClosed deal
EA commitment per year$15M$12.7M
Copilot coverage, year one60 percent of users20 percent, 40 by year three
M365 SKU mixE5 across the estateMixed E3 and E5
Total savings over termBaseline$3.8M

The situation

Eight thousand users, almost all of them on Microsoft 365 E5. E5 is a fine product and a poor default. It bundles advanced security, compliance and analytics that a minority of any workforce actually uses, and it is priced accordingly.

Azure carried the firm's service delivery platform. Copilot had been rolled out across a broad slice of the user base. Dynamics 365, Power Platform and GitHub sat alongside, each with its own quiet growth.

Consumption had grown across the previous term to roughly 12 million dollars a year. Microsoft had that number, along with the 2026 price increase as a ready made reason for the next one to be larger.

What Microsoft proposed

Microsoft put 15 million dollars a year on the table for three years. The increase was built from four assumptions, and each one deserved an argument.

E5 would stay estate wide. Copilot would reach 60 percent of the user base in year one. The Azure MACC would be sized to an optimistic consumption curve. The 2026 price increase would apply broadly rather than be negotiated line by line.

None of these are unreasonable opening positions. They are simply the vendor's preferred version of the customer's future, and no one had yet put the customer's version next to it.

What the numbers actually showed

We rebuilt the position from the firm's own telemetry and deployment plans. Five commercial dimensions carried the analysis, and the reconstructed number came out roughly 20 percent below the Microsoft proposal.

  • M365 SKU mix. Segment the user base by actual security, compliance and analytics need, then license each segment for what it uses.
  • Copilot trajectory. Model adoption against measured productivity uplift rather than against a target coverage percentage.
  • Azure MACC. Size the commitment to an 85 percent confidence consumption forecast, not a full confidence one.
  • The 2026 price increase. Treat it as a negotiable line in this agreement rather than an external fact.
  • Contract terms. Test flexibility and risk allocation against what the business actually needs.

The SKU work was the largest single lever. Once the population was segmented, the number of users who genuinely needed E5 turned out to be a fraction of the estate.

We also costed the alternative. Google Workspace was a credible option for a defined slice of the user base, and pricing it properly turned a captive renewal into a competitive one. See the Google Gemini enterprise licensing guide for the comparison.

The eleven moves

Eleven moves carried the negotiation. The SKU and Copilot work set the number, and the terms work protected it.

  1. Segment the user population. Split by high security, high compliance, high analytics and general productivity need before pricing anything.
  2. Move to a mixed E3 and E5 estate. E5 for the populations that use its capabilities, E3 for everyone else.
  3. Stage the Copilot rollout. Tie coverage to measured uplift across three to four years rather than a year one target.
  4. Negotiate the Copilot rate against the staged curve. A smaller committed population does not have to mean a worse unit price.
  5. Size the Azure MACC honestly. Anchor to an 85 percent confidence consumption forecast.
  6. Win explicit true down rights on the MACC. Commitments should be able to move in both directions.
  7. Negotiate the 2026 price increase. It is a line in your agreement, not a law of physics.
  8. Size Power Platform to the deployment plan. Not to the licensing model's preferred shape.
  9. Size Dynamics 365 the same way. Actual rollout plan, actual user counts.
  10. Cost the alternative properly. A priced Google Workspace option for a defined population makes the competitive position real.
  11. Negotiate the contract terms. Flexibility and risk allocation outlast any discount.

The counter proposal

The counter landed at 12.7 million dollars a year against the 15 million opening. Every element traced back to the firm's own deployment data, which is what made it hold.

It carried the mixed E3 and E5 estate, the staged Copilot curve, an Azure MACC sized to the 85 percent forecast with explicit true down rights, a negotiated position on the 2026 price increase, and right sized Power Platform and Dynamics 365 counts.

Presenting it as one package mattered. Separate asks invite a vendor to concede the cheap ones and hold the rest. See the 2026 Microsoft price increase analysis for that line in detail.

The close

Contract finalisation ran four weeks. The commitment held at 12.7 million dollars a year across three years, with the SKU mix, the Copilot curve and the MACC sizing all landing where the counter had put them.

The MACC true down rights were written in explicitly, which matters more than it sounds. A commitment that can only ratchet upward is not a commitment, it is a floor with a friendly name.

Power Platform and Dynamics 365 were sized to the actual rollout plans, and the contract terms were rewritten around the firm's real flexibility needs. See the Azure MACC negotiation notes and the M365 E3 versus E5 comparison.

The outcome

  • EA commitment. 12.7 million dollars a year against a 15 million dollar opening. Roughly 15 percent below in year one.
  • M365 SKU mix. Mixed E3 and E5 matched to actual security and compliance need, cutting the productivity run rate materially.
  • Copilot. Staged at 20 percent of users in year one, expanding to 40 percent by year three.
  • Azure MACC. Sized to an 85 percent confidence consumption forecast, with explicit true down rights at renewal.
  • 2026 price increase. Negotiated against the firm's own agreement rather than applied as a blanket uplift.
  • Contract terms. Improved risk allocation and flexibility across the agreement.
  • Total saving. 3.8 million dollars across the three year term.

What to do next

If a Microsoft EA renewal is ahead of you, work through these in order.

  1. Segment your user base by actual security, compliance and analytics need before anyone discusses SKUs.
  2. Count how many users genuinely consume E5 capabilities. On most estates it is a minority.
  3. Measure Copilot uplift on the population that already has it, and let that evidence set the rollout curve.
  4. Build an Azure consumption forecast at 85 percent confidence and treat it as your MACC ceiling.
  5. Put the 2026 price increase on the negotiating table as a line item rather than accepting it as context.
  6. Cost a real alternative for a defined slice of users, and open the conversation at least sixteen weeks out.

Lessons learned

Three lessons travel from this engagement to any Microsoft renewal.

  1. SKU mix is the buyer's decision. A uniform E5 estate is a licensing convenience, not a security posture. Segment the population and license each part for what it actually uses.
  2. Copilot should follow evidence, not enthusiasm. Coverage targets are a vendor metric. Measured productivity uplift is a buyer metric, and it is the one that should set the curve.
  3. Commitments need to move both ways. True down rights on a MACC cost nothing to ask for at signature and are close to impossible to add later.

The full method is set out in our Microsoft EA Renewal Playbook, the Microsoft Copilot licensing guide 2026, and the M365 E3 versus E5 comparison.

For the cloud side, see the Azure MACC negotiation notes and the Azure cost optimization playbook.

Related reading: the US professional services EA case study, the Canadian manufacturer EA case study, the Brazilian bank EA case study, and the CIO playbook for the 2025 to 2026 Microsoft licensing model.

Microsoft EA Renewal Playbook

Forty pages. The full EA renewal from the Microsoft practice.

The eleven moves, the discount tier, SKU segmentation, the Copilot staging curve, Azure MACC sizing, and the contract terms that matter at every step of an EA renewal.

Used across more than five hundred enterprise clients. Independent. Buyer side. Built for IT procurement leaders running the next EA cycle.

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$3.8M
Saved over EA term
8,000
Users on EA
11 moves
Buyer side moves
16 weeks
Engagement duration
100%
Buyer side

Microsoft wanted fifteen million a year, E5 for everyone and Copilot on sixty percent of staff by Christmas. Redress showed us how few people actually used E5, staged Copilot against real uplift, and priced a Google option. We saved three point eight million.

Chief Information Officer
Chicago IT services firm
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