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Don’t Get Locked into Microsoft Support Negotiations—Again – 3rd Party: A Microsoft Support Show (ep8).

Think you have to renew with Microsoft Unified Support? In this episode of 3rd Party, we reveal how procurement leaders are cutting costs, gaining leverage, and taking back control — without giving up support quality.
Mike Jones
Written by:
Mike Jones
Published May 22, 2025
Don't Get Locked into Microsoft Support Negotiations—Again – 3rd Party: A Microsoft Support Show

Microsoft wants you to think you don’t have options when it comes to Unified Support. But the truth is, you do.

In the latest episode of 3rd Party: The Microsoft Support Show, we break down what every procurement leader needs to know before stepping into another round of painful, expensive negotiations with Microsoft. We sit down with Chris McCullough, VP of Global Sales at US Cloud, to expose the realities of negotiating with one of the most powerful sales organizations in the world — and how you can flip the script.

From late-stage bundling tactics to the infamous “Microsoft Support Tax,” this episode is a crash course in reclaiming negotiation control. Chris lays out a playbook for breaking down opaque pricing while avoiding last-minute lock-ins, just by using third-party quotes as leverage — even if you end up staying with Microsoft.

Here’s the bottom line: alternative support providers like US Cloud deliver faster service across the full Microsoft stack, at 30-50% less cost. Time is running out if your Unified contract is up for renewal, so now is the time to act. Don’t let Microsoft run the clock on your decision. Get informed, get leverage, and get the free quote that could save you millions.

Read the Full Transcript Here

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Tipper O'Brien

Hi, everybody. Welcome to 3rd Party, a Microsoft support show. Today we’re joined by VP of Global Sales here at US Cloud, Chris McCullough. We’re talking today about how to negotiate with Microsoft the easy way, which, Chris, there really is no easy way. Spoiler alert, guys: typically, it’s an extremely difficult process for procurement officers to solve for what the process is like when negotiating with Microsoft.

You know, there’s a reason why they’re one of the world’s most respected marketing and sales organizations. The Microsoft team is smart—they know what they’re doing. It’s very typical for procurement folks to see late offers, to see offers that require bundling, to see no budgeting whatsoever on offers that are made.

But we’re going to talk about a few ways that procurement folks can impact those discussions in a positive way.

Chris McCullough

Fantastic, Tipper. It’s good to be here with you, and happy to talk about it. It is a convoluted process. It’s a long process. It can be painful at times, so let’s go through it.

Tipper O'Brien

Yeah, let’s get into it. So tell me: what are some of the big challenges that large organizations face when negotiating with this behemoth that is Microsoft?

Chris McCullough

Microsoft is the giant in the room—you know it. Fortune 500 companies, large enterprises… when negotiating with Microsoft, they still hold a lot of the cards, and the Unified Support piece is often the elephant in the room. It’s a tough one to talk about for a couple of reasons.

The support isn’t great. A lot of feedback we get from incoming clients is about problematic service, changing price structures year over year—it’s a tough negotiation point. There are several pitfalls throughout the process, and overall, it’s a long, convoluted, not-so-fun experience.

Tipper O'Brien

And this is something procurement folks have to do year in and year out. They put a lot of time into negotiating, get a deal signed that they’re happy with—and then they have to do it again twelve months later.

Chris McCullough

Exactly. There’s a lot of fatigue involved. You fight the battle one year, maybe come to a conclusion, then pretty soon you’re at it again. And people’s technology footprints aren’t shrinking—they’re growing, which drives Unified Support costs up.

Each year, clients who come to US Cloud have the same issues: getting the best price, the best offering, then having to renegotiate. But with our model—how we organize, price, and lock in rates for multiple years—there’s a lot less stress on that ongoing conversation.

Tipper O'Brien

Okay, so Chris: what are some of the challenges that large organizations face when going into these negotiations with Microsoft?

Chris McCullough

Well, if Microsoft is the giant, then Unified Support is the elephant in the room—nobody wants to address it. IT teams hate the support experience, and procurement teams hate the painful, recurring negotiation process. That’s why Unified often gets bundled separately or left off entirely: Microsoft finds it hard to tackle head-on.

Tipper O'Brien

So, in fact, they bundle it with something else or shuffle it off to one side because the situation isn’t good?

Chris McCullough

Exactly. Bundling is a big part of it. There’s an old adage: “Where there’s mystery, there’s margin.” If you don’t truly understand pricing per product, per service, or per technology delivery, there are too many moving pieces in those agreements.

Tipper O'Brien

Okay, I’m a procurement leader, maybe a little worn out—I’ve done three, four, or five deals with Microsoft. What can I do better this year to make my negotiation a bit easier?

Chris McCullough

It’s all about options. You need to evaluate what third-party pieces look like—what US Cloud offers, how we’re organized differently, what our deliverables are versus Microsoft Unified, and how it’s priced. The more ammunition you have, the better you’ll negotiate—whether you stay with Microsoft or move to something entirely different.

Start those discussions early. Include not only your sourcing team but your IT stakeholders. Talk to every individual supporting the technologies that matter to you, and dive into deep preparation.

Tipper O'Brien

Big piece of the game here: what are some of the easier things I can prepare that I can have in hand when I get into that discussion with Microsoft?

Chris McCullough

Start by looking at your actual usage over the past year. Understand your ticket history—what technologies you most often work with Microsoft to support.

Tipper O'Brien

So preparation is key. As a procurement leader, what research should I do before I go into that conversation with Microsoft?

Chris McCullough

Several things. Look to independent organizations like Gartner, InfoTech—industry giants tracking technology vendors. You’ll find a lot of analysis around third-party support. In preparing for negotiations, it’s important to understand your own technology needs.

What support have you consumed over the last year? What types of tickets are you placing daily? There’s a usage report in your Microsoft portal—get a baseline of your needs, because your technology initiatives and adoption from Microsoft may be growing. Ask: Is my support need changing?

Tipper O'Brien

Okay, let’s assume I’m prepared: I have my usage report, maybe even a quote from a third-party. What should I expect Microsoft to push on when they come to the table?

Chris McCullough

Watch their priorities—they’ll tell you a lot about their agenda. Are they pushing cloud spend? Copilot adoption? New technologies that might not make sense for your roadmap? Those are bargaining chips. Break them out as separate proposals rather than having everything bundled together.

Tipper O'Brien

We know Microsoft has a history of co-terming or bundling an Enterprise Agreement with Unified Support—or the so-called “Microsoft Support Tax.” What are some ways to unbundle that agreement? What is Microsoft focused on that I can use to my advantage?

Chris McCullough

Microsoft is focused on increasing Azure spend, Copilot adoption, new technology uptake. If those align with your roadmap, absolutely use them as bargaining chips—treat each as a separate proposal. The more bundles you unravel, the less mystery, and you can see if it’s really benefiting you or if the cost is right.

Tipper O'Brien

So let’s say you have a deal on the table from Microsoft—who can you look to for additional help?

Chris McCullough

Organizations like Gartner, InfoTech—their whole business is helping you navigate what’s in front of you. Directions on Microsoft is another fantastic resource for Microsoft-specific questions. How do I negotiate? What trainings do you offer to help me and my team? Use those resources to get the most out of these conversations and the relationship going forward.

Tipper O'Brien

Today’s conversation has really focused on preparation: being clear on your current and future usage, having a third-party quote for support, and understanding Microsoft’s priorities so you can consider unbundling.

What other ways can US Cloud help procurement leaders go through this process?

Chris McCullough

Get a quote—period. Eighty percent of IT procurement officers who come to US Cloud get a better deal. Period.

You might just go get a quote from us—80 percent get a better deal. Use our Azure Optimization tool to cut your Azure spend, refocus in other areas, and leverage our partner network for negotiation and execution support.

It’s simple: come get the information, go through the process, get a quote. Over 80 percent of procurement leaders who come to us save money—whether they stay with us or even if they stay with Microsoft. And our Azure Optimization tool can save 30–50 percent on Azure spend.

When you come to US Cloud, pull up the hood: see how your Azure spend is organized. We’ll find savings, identify waste—it’s time well spent.

And lastly, there’s our partner network—use them for additional resources and negotiation tactics. There are so many resources out there, and US Cloud can point you in the right direction to make this year’s experience less painful.

Recently we worked with a sourcing director in the U.K. who was at her wit’s end—conversation after conversation with Microsoft, hours on the phone. She needed long-term relief.

We proposed a multi-year solution with US Cloud: very little fluctuation in rates, depending on needs and organization. What made sense for her was comfort for the next three years, rather than going back to Microsoft after her team expanded their footprint and saw wildly fluctuating pricing.

Tipper O'Brien

What were her savings like?

Chris McCullough

At least fifty percent—perhaps fifty-two percent?

Tipper O'Brien

And what does that amount to in…

Chris McCullough

Dollars? In her case, it was millions of dollars—this was a multinational company.

Tipper O'Brien

Millions of dollars every year, or over the span of?

Chris McCullough

This was one year. Over a three-year term, that’s tens of millions of dollars saved on support. And it’s not just a pricing play—US Cloud is a value play. We organize our service and support differently, above what clients tell us they experience with Microsoft day in and day out.

It’s a value and quality play, locked in for three years with the comfort of not having to fight that fight again in eight months. We want to make it easy for you.

We also worked with a large global bank—conversations for months, massive trust in us, huge savings. But in the end, Microsoft came back with a fantastic offer, and the bank stayed with Microsoft. That’s OK—sometimes Microsoft will win that negotiation. But often, clients will move to us for the experience we provide.

Tipper O'Brien

You mean if you go back to the mothership…

Chris McCullough

If you go back to the mothership? It’s so hard to leave Microsoft—canceling things like Premier Support for Partners is nearly impossible. They’ll come back with $5-a-month offers, then $2-a-month. They keep at you until it makes sense to stay.

But what happens is you’re exposed to our team, have conversations, and next time we’ll be positioned much better as your future partner.

Tipper O'Brien

Awesome. Well, thanks so much for your time, Chris.

Thanks again for joining us on 3rd Party: the Microsoft Support show. Hopefully some of the tips you learned today will help in your upcoming negotiation with Microsoft. As always, feel free to reach out to us at uscloud.com—we can help with those negotiations and give you a valuable quote for your next discussion with Microsoft.

Mike Jones
Mike Jones
Mike Jones stands out as a leading authority on Microsoft enterprise solutions and has been recognized by Gartner as one of the world’s top subject matter experts on Microsoft Enterprise Agreements (EA) and Unified (formerly Premier) Support contracts. Mike's extensive experience across the private, partner, and government sectors empowers him to expertly identify and address the unique needs of Fortune 500 Microsoft environments. His unparalleled insight into Microsoft offerings makes him an invaluable asset to any organization looking to optimize their technology landscape.
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