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How Onebrief Is Fixing Military Planning With Software

Grant Demaree was a junior US Army officer watching military planners pass around Word docs and PowerPoints during the 2014 Ebola crisis when he realized something: the military’s most critical decisions were being made with outdated tools and slow, legacy workflows. That insight led him to build Onebrief—a platform now used by military headquarters worldwide to dramatically accelerate their planning. But to get there, he had to figure out how to get the military to actually buy software. Grant sat down with YC's Brad Flora to share how they did things that don’t scale to get their first users, closed their first deal with a government credit card, and turned an offline, Navy-approved laptop into a $650M company helping military teams make faster, smarter decisions. Learn more about Onebrief: https://www.onebrief.com Apply to Y Combinator's Summer 2025 batch: https://www.ycombinator.com/apply

Brad FlorahostGrant Demareeguest
May 13, 202524mWatch on YouTube ↗

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  1. BF

    Grant Demaree is a former US Army officer and the co-founder of Onebrief from YC Summer '21 batch. They're creating software to help dramatically speed up military planning

  2. GD

    What we're doing is, on a, on a per dollar basis, the most important thing happening in defense tech in the world.

  3. BF

    Today, we're gonna talk with him about what he's learned selling software to what some might consider the most complicated, hard-to-crack customer in the world, the United States military. [upbeat music] Thanks for joining us today.

  4. GD

    Thank you very much, Brad.

  5. BF

    So what is Onebrief?

  6. GD

    So we make software for operational military planning. Every military headquarters around the world, from a giant combatant command like US Indo-Pacific Command, down to something small like a battalion, um, almost everything they do has a, has a plan. Um, that could be very detailed, like how do we defend Taiwan, or, you know, something, a, a bit more casual, like what are we going to do tomorrow. And the process, it, it takes a long time. It drives almost every military decision, and if we can make it faster and smarter, well, it has a, a huge effect on how well the military does.

  7. BF

    And so you guys have been at this for a few years now, and you've started to achieve, like, pretty epic scale. Um, what can you tell us about, like, how big the company's got, um, valuation, revenue, size of the team, to put it in perspective for everybody?

  8. GD

    Today our, our software's in use in quite a lot of, of military headquarters worldwide. Um, we're growing usage, uh, 2.75x quarter over quarter right now, um, which translates to about a, a 57x, um, year over year growth rate. And, uh, we're at about 144 people, um, and we just raised a Series C at a, uh, 650 million valuation.

  9. BF

    How have people in the past or up to this point done military planning from a technical standpoint?

  10. GD

    Uh, well, almost all Word and PowerPoint.

  11. BF

    Mm.

  12. GD

    Um, there's actually been a huge number of attempts to make it not be Word and PowerPoint, but, uh, those products are pretty sticky. So if I'm trying to make, like, a, a, a giant military plan, I'll often make hundreds of slides, um, and I'll, you know, email them back and forth across every contributor, which, you know, could be 12 different headquarters, and I'll ultimately produce this, uh, large Word document called an operations order, or in, in other situations, a base plan.

  13. BF

    Tell us a bit about how it works. What's the actual user experience like for people using Onebrief?

  14. GD

    The overall idea is how fast can a team across a bunch of different military commands, um, get to a plan, whether short range or long range or mediating crisis, make it be really fast. We built the system around cards, which is probably really familiar to you, and you're using a bunch of reusable cards, where a card might be, you know, a fact about the situation, um, might represent a military unit, might represent a task. And you're using these cards to build all your outputs, like a sync matrix, a operations order, which is the, the Word document, or maps that present these cards on the map, or all sorts of other outputs that are using the same, the same blocks of data. And when you change one, it, it updates, uh, you know, all the others, and, you know, you're embedding portions of one document in another. So the largest type of military plan is, is called an O-plan. Um, these are for the, the really big ones. Think defense of Europe. Um, those take about two years to write if everything goes perfectly.

  15. BF

    You bring Onebrief into this equation. What's, uh, you know, are we able to compress these times down from two years? Is it a much simpler document? What's the benefit?

  16. GD

    The one I'm most proud of, um, there was a course of action that came out of a major plan against a core US adversary, and the, uh, the planners are presenting it to the chief of staff at a major Onebrief customer, and the chief of staff says, "No, no, no, this course of action is terrible. It's not what you're gonna do. You need to go change it." And that normally would create, like, several weeks of work. In three hours, they had changed the entire thing, new map overlays, new sync matrix, new written base plan, new slides, presented it, commander signs it, no further changes. That was using Onebrief.

  17. BF

    So where did Onebrief start, and what were you doing at the time?

  18. GD

    I was a, uh, US Army officer. Um, had the idea as a very junior lieutenant straight out of West Point. I was in Liberia part of the 2014 Ebola epidemic. Now, this was my first military experience, which actually turned out to be, to be really good to, like, see this with fresh eyes. I was actually working Ebola data out of the Ministry of Health, but it was attached to their J5, which is responsible for military planning, and that meant I, I got to see how military planning at a large headquarters worked, which, uh, of course, I thought like, "Oh, this is so cool. I'm, I'm really happy to see behind the curtain." But I ultimately felt that it could've been a lot more effective than it was-

  19. BF

    Mm

  20. GD

    ... where watching people, like, pass PowerPoints around the headquarters and, uh, uh, eventually make decisions months later than we could have made the decisions, so okay, this is, this is really not optimal. I was in a- another headquarters a couple years later, um, this time I, I think with a more informed perspective, having seen this once. I was a, a little bit more senior. Um, this was, uh, CJTF-OIR, so the theater headquarters, um, out of Baghdad for Iraq and, and Syria against ISIS, and I saw other operational planning teams there and said, "Well, this is, this is a pattern. Um, this happens in a lot of places. This is, you know, the core driver of military decisions, and I think fixing military decisions is, is the most important thing we can do in defense tech, so I'm gonna get out of the Army and, uh, try to fix it."

  21. BF

    One thing that I think is interesting here is, uh, for people that maybe have an idea, you have this genesis of an idea of something that I could build and maybe sell and, and provide back to the military, I think it's pretty intimidating to a lot of folks. Maybe there's other people out there that have had ideas like this, but they don't even know where to begin. Talk to us a bit about how you understood or mapped the opportunity such that, um, it wasn't just, like, selling to a giant monolith. We're gonna sell to the Army. Um, I think it's actually a lot more nuanced than that, and there's many different ways that you can kind of work your way into the, into the, um, the defense ecosystem.

  22. GD

    Yeah, so, uh, basically every military, and especially the US military, is a huge number of different organizations that control their own budgets. And, and these are often like, you know, eight or nine and, and sometimes 10-figure, uh, you know, budgets for these individual headquarters.

  23. BF

    Mm.

  24. GD

    And in the US there's, there's about 1,200 commands that, that need our product. Basically what this means is that you don't, at least initially, have to sell to DOD as one giant customer.

  25. BF

    Mm.

  26. GD

    I mean, you can actually sell to the individual command that most needs your product, which is so much faster and easier and keeps you a lot closer to the end user.

  27. BF

    How many people at a given headquarters do you usually have to actually present to or convince?

  28. GD

    Well, our first deal was one. Um, and now these are, you know, pretty standard e- enterprise sales where there's, you know, a, a, a committee of people who need to, you know, be persuaded and are, are stakeholders. But I don't think that's helpful-

  29. BF

    Mm-hmm

  30. GD

    ... to say in a, you know, very early stage founder doing defense tech. We were able to get the initial sale on a government purchase card. So there's these basically credit card ... I mean, they are credit cards that, uh, a lot of military officers and NCOs have, um, if their organization has something of a slush fund, and they can buy things up to, depending on the place, sometimes it's up to $25,000, and just buy it.

Episode duration: 24:36

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