Hey, I'm Dan! I invest in startups at Madrona and write the DL, a weekly newsletter about tech in the Pacific Northwest

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How to Close a $10B Deal

A couple weeks ago, the Department of Defense released a 317 page report on the $10B JEDI contract. While the report was meant to investigate misconduct, it’s also a great look at how the digital transformation and procurement processes work at a large organization.


Here’s a summary of what happened over the 10 year process:

  • Dec 2011 - DoD begins developing their cloud transition strategy
  • Jan 2017 - Secretary Mattis learns the CIA moved to the cloud
  • Aug 2017 - Secretary Mattis visits tech companies in WA and CA
  • Oct 2017 - DoD releases the Cloud Request for Information (RFI)
  • Jul 2018 - DoD releases the final JEDI Cloud RFP
  • Dec 2018 - DoD publishes their Cloud Strategy (only took seven years!)
  • Apr 2019 - Source Selection officials finish rating RFP responses
  • Sep 2019 - DoD hosts meeting with members of Congress to hear their concerns about the JEDI contract
  • Oct 2019 - Microsoft wins the JEDI contract (two years after the RFI)


So basically, the timeline for a digital transformation is several years to research the market and speak to people who have done it before, another year to write strategy docs and meet potential vendors, and one year to refine strategy, review proposals, and get stakeholders on board.


The report also has some fun details like what Secretary Mattis and Jeff Bezos talk about at dinner. Apparently, Mattis loved Bezos’s thoughts on “failing fast,” and how in uncertain environments one should embrace failure and not worry about intelligent or cheap failures. Good advice!


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