Sales Win: How Microsoft Won the $10 Billion JEDI Contract
What You Can Learn from Microsoft’s Strategic Approach to Securing High-Stakes Deals
In 2019, Microsoft pulled off a landmark sales win: the $10 billion Joint Enterprise Defense Infrastructure (JEDI) contract with the U.S. Department of Defense. The win was not just about the size of the deal it was a masterclass in playing to strengths, understanding the customer’s needs, and building lasting relationships. Microsoft beat out fierce competition, including Amazon, to secure this transformative opportunity. Today, we will distill the key lessons from this historic deal into three actionable insights you can apply to your sales strategy.
Play to Your Strengths
Microsoft leaned heavily on its reputation for secure, scalable, and reliable enterprise solutions, positioning its Azure cloud platform as the perfect fit for the Department of Defense’s needs. Instead of focusing on what competitors offered, Microsoft showcased why their solution was uniquely suited for the job. You want to do the same thing. Instead of focusing on what your competitors are doing or how their funding rounds are going, just focus on your strengths and the value you bring.
Consider the following:
Highlight what makes your product the best fit for your customer’s specific needs.
Focus on benefits that solve the customer’s problem, not just general features.
Tailor your pitch to demonstrate how your solution aligns with their goals better than anyone else’s.
By owning its strengths, Microsoft framed Azure as the obvious choice—a strategy every founder can use to differentiate their offerings.
2. Understand the Customer’s Landscape
A deep understanding of the Department of Defense’s requirements gave Microsoft the edge. They didn’t just sell a product—they addressed the DoD’s need for a secure, future-proof cloud solution. Microsoft anticipated potential objections and positioned Azure as the natural partner to achieve the DoD’s goals.
Consider the Following:
Research your customer’s pain points and broader industry trends thoroughly.
Focus on customers that have the problem you are setting out to solve. At least at the beginning this will be key to your success.
Anticipate objections and proactively address them in your pitch.
Also consider asking your customer what their key challenges are before the sales call.
Demonstrate that you’re not just a vendor but a partner invested in their long-term success.
When you show customers you understand their business as well as (or better than) they do, you build trust and make it easier for them to choose your solution. You also make it easy for them to see the value you bring since you understand the problems they are facing.
3. Build Trust and Credibility
Microsoft’s long-standing relationship with government agencies played a pivotal role in its JEDI win. By consistently delivering on past projects, they built trust and positioned themselves as a reliable partner for the Department of Defense. I’ve covered this on other big sales wins we’ve talked about. The key relationships with current and future customers will also be a part of a big win. I’ve seen it again and again in my career. Those that have the key relationships, get the information and win the RFP.
Consider the Following:
Focus on building credibility and trust over time, not just during the sales process.
This has to start long before any request for proposal (RFP).
Fine ways to connect with your future customers and understand their problems outside of a regular sales call.
Develop relationships with decision-makers and influencers within your target accounts.
Make sure you understand who are decision makers and who are influencers.
Both groups of people are important to have relationships with.
Use past successes with similar clients to bolster your reputation.
Using case studies of your successes as marketing material can help find these similar clients.
The trust Microsoft built through years of consistent delivery created a foundation that even stiff competition couldn’t shake.
Microsoft’s $10 billion JEDI contract wasn’t just a financial victory it was a strategic masterstroke that showcased the power of playing to strengths, understanding the customer, and building trust. Whether your sales are in the thousands or billions, these lessons can help you secure transformative wins and set the stage for long-term success.
Action Step:
Take 30 minutes this week to reflect on your biggest sales opportunity:
What unique strengths can you emphasize to set your solution apart?
How well do you understand your customer’s specific challenges?
What relationships can you strengthen or leverage to build credibility?
Write down three actionable steps you can take this week to position yourself as the go-to solution.
Additional Reading:
“How Microsoft Outmaneuvered Amazon for JEDI” – Forbes
“Building Long-Term Client Relationships” – Harvard Business Review
“The Art of Competing Against Bigger Players” – Sales Hacker