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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during the 2014 Ebola crisis when he realized something: the military’s most critical decisions were being made with outdated tools and slow, legacy workflows.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 ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:09

    Onebrief’s mission: speeding up operational military planning

    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.

  2. 1:09 – 1:46

    Company traction and scale: adoption, headcount, and Series C

    1. 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?

    2. 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.

  3. 1:46 – 2:21

    The legacy workflow: Word, PowerPoint, and emailed slide decks

    1. BF

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

    2. GD

      Uh, well, almost all Word and PowerPoint.

    3. BF

      Mm.

    4. 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.

  4. 2:21 – 3:24

    How Onebrief works: cards, shared data, and multi-output planning

    1. BF

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

    2. 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.

  5. 3:24 – 4:06

    Compression in practice: rewriting a major course of action in hours

    1. 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?

    2. 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.

  6. 4:06 – 5:38

    Origin story: seeing planning dysfunction during Ebola and OIR

    1. BF

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

    2. 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-

    3. BF

      Mm

    4. 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."

  7. 5:38 – 6:52

    Understanding the customer: selling to many commands, not one monolith

    1. 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.

    2. 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.

    3. BF

      Mm.

    4. 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.

    5. BF

      Mm.

    6. 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.

  8. 6:52 – 8:31

    Early sales hack: government purchase cards to bypass procurement drag

    1. BF

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

    2. 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-

    3. BF

      Mm-hmm

    4. 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.

    5. BF

      Mm.

    6. GD

      Very little process, very little contracting, and it's a bit of a hack to avoid the contracting process because if you're coming in and, and d- don't know how to do contracting, um, you can just get in the headquarters. So it, it actually helped us a lot by closing a small sale in, you know, relatively little time just to get physically in the headquarters to be exposed to users.

    7. BF

      Yeah, that's a great hack. We're always telling YC founders, uh, to find some simpler way to validate that people will actually pay for the product that they're building. And so instead of going through a multi-month procurement, you're able to get one person to make a decision and put it on a card. When you first set out to start working on this, you decided, "Okay, I'm gonna go build a company," what was the first thing that you did to kind of figure out what exactly you needed to build and what the customers actually wanted from you?

  9. 8:31 – 9:14

    Early product misstep and correction: build less, interview more

    1. GD

      We started with the, with the, the wrong answer, which is started just building. I don't totally regret it because it's how I got my co-founder, who turned out to be, like, truly excellent. I started making these, like, clickable mock-ups of here's what I think the product needs to look like, and then actually, like, wrote an early version of the product in MATLAB 'cause it's the only thing I knew. And it was something of a show of seriousness of like, "Hey, we, we really want to build this thing that's going to fix, uh, you know, military planning."

    2. BF

      Talk to me about the user interviews for a minute. Like h- who were you reaching out to?

    3. GD

      W- we basically reached out to every stakeholder in military operational planning. It was about 200 interviews, and, uh, well, it was, it was really, really good, and, uh, we were pretty wrong to think we didn't need to do that.

  10. 9:14 – 10:45

    Getting real feedback without access: Saturday planning exercises

    1. BF

      How did you get early users for this thing? I know you guys did a bunch of, like, um, things that don't scale to get people into your early software. Tell us about some of those.

    2. GD

      So the problem we had to solve is we couldn't get access to real users.

    3. BF

      Mm-hmm.

    4. GD

      This is before I had any contract. This is before we were in the room wi- in, in the military headquarters.

    5. BF

      Mm-hmm.

    6. GD

      There were just too many barriers to get any usage-

    7. BF

      Yeah

    8. GD

      ... and see how this worked.

    9. BF

      This is like the first year or so after you started working on this.

    10. GD

      That's right. What we ended up doing is cold LinkedIn messaging a bunch of, uh, military planners-

    11. BF

      Mm-hmm

    12. GD

      ... usually majors through colonels, and said, "Come to my all-day Saturday exercise."

    13. BF

      Mm.

    14. GD

      "We'll pay you, but you need to be here for eight hours."

    15. BF

      Okay.

    16. GD

      And we put together this, like, pretty robust military scenario. Like, I'd, I'd spend, like, almost 100 hours writing these scenarios.

    17. BF

      Mm.

    18. GD

      And I'd put them into two teams and say, "You six are gonna solve this military scenario in the old way with Word and PowerPoint, and you six are a team and y- you're gonna solve it in this, like, proto version of Onebrief. And we're all gonna watch you, and we're gonna make the product better."

    19. BF

      What kind of feedback were you getting, or what sort of lessons were you learning from these exercises? I imagine throwing these people at your product in its early stages was maybe a little scary and a little sobering at times.

    20. GD

      So the response was a lot better than we thought. So we tried, like, a whole bunch of go-to-market things already that were ... They didn't work that well, and this was the first time where the response was genuinely great-

    21. BF

      Mm

    22. GD

      ... where people were like, "I am very excited. Can I introduce you to people in my headquarters?"

    23. BF

      Mm.

    24. GD

      "Can I help you?"

  11. 10:45 – 12:35

    First real foothold: embedding at Pacific Fleet via a warm intro

    1. BF

      Okay. So you did these 200 customer calls. You're doing these exercises with planners. How did you go from that to actually getting your first proper contract?

    2. GD

      I had a phone call via a warm intro, um, with this gentleman, Captain Dave Fields at US Pacific Fleet, and actually didn't know he was as big of a deal as he was when I had the, the phone call. So I, I told him what we were up to, and the first thing he says is, "I've actually evaluated at least 10 attempts to solve this problem. They've all been terrible." And I could tell this was, like, a, you know, a sharp person who really cared about it, and we ended up chatting on, like, this first discovery call for about two hours on the phone. I think the, the level of honesty about, like, what we did and did not know was pretty helpful, um, in, like, building some, some real trust. But he came out of it saying, "This is, this is promising." Then I said, "Great. Can I embed in your headquarters? I don't wanna just stay there. I wanna stay there for three months. I wanna try a proto version of our product on some of your operational plans." And I was like, "Just put in a government purchase card for some, like, nominal amount of money."

    3. BF

      Mm.

    4. GD

      And he was just like, "Okay, let's do it."

    5. BF

      What else do you think might have been things that kind of persuaded him to give you some extra time and to really bet on you guys for this?

    6. GD

      I think there were some creative parts of our approach that weren't take the existing government process and put it directly into a product 'cause we had this presumption the existing process was, was bad and needed to change pretty dramatically. Um, and we would build a product around the future in- instead of the past. You know, sometimes people can just, like, detect a certain level of, like, energy and determination where like, oh, this is, this is real. I think the ask of, "Can I embed and just get it done?" is a more earnest ask than, "Can you give me money?"

    7. BF

      How did that lead into an actual contract eventually?

  12. 12:35 – 15:51

    Security and deployment barriers: ATO, SCIF access, and “one-laptop” hacks

    1. GD

      So I was away for, it was a little over 250 nights that year, most of them to Pearl Harbor, um, Hawaii. And we embedded around, around two plans. One was this, uh, large exercise called Pacific Fury. It's, like, one of the largest exercises in the Navy. It's really important. Our product was used for, like, a fraction of 1% of it.

    2. BF

      Mm.

    3. GD

      But it was still real, and it was still the first time we'd been used for, for anything real. And there was actually, like, a pretty interesting barrier to entry, which is a, a, a theme in defense. So they can't use software that doesn't have an authority to operate, especially not for classified work 'cause, like, these are, are secret and top secret. Uh, 'cause like-

    4. BF

      What does authority to operate mean?

    5. GD

      Uh, authority to operate is the, uh, accreditation that-

    6. BF

      Okay

    7. GD

      ... like, lets you put software on their intranet.

    8. BF

      I see. How does one get this?

    9. GD

      The first thing you need is the contract, and the second thing you need is to work through some administrative steps to get approved. There's actually, like, a, a lot of art to it. Like, there's ways you can do it that will cost you many, many millions and take you many years. There's actually a lot of defense tech companies that don't have one after being in business for more than five years.

    10. BF

      Mm.

    11. GD

      What we did initially was just circumvent the problem. We knew too little. We were too early to g- to figure out ATO. And I believe if we'd tried at that stage, it would've been this all-consuming problem that, uh, would have meant that we never found product market fit.

    12. BF

      Mm.

    13. GD

      So what we did to get around the problem is, um, deploy our software on one computer.

    14. BF

      Okay.

    15. GD

      My computer.

    16. BF

      All right.

    17. GD

      And went to their, their N6, which is their word for IT department, and said, "I wanna bring this one computer into your SCIF," which is their word for a secure facility that handles, like, top secret and above information. And we actually got to yes on that. Um, but we got to yes by agreeing that the Wi-Fi was disabled, Bluetooth was disabled, and the laptop would become Navy property to dispose of and destroy when we were done.

    18. BF

      That's amazing.

    19. GD

      So, so they let us do it, and I was the only user. So we, we weren't at the point that any military planner, like, wanted to change their workflow and, like, use this thing.

    20. BF

      Mm-hmm.

    21. GD

      Which would just be, like, a totally worse experience anyway 'cause it's not connected to the network. You can't even, like, email your results. You can't share your results. It's collaborative software with no collaborators, uh, which sounds terrible. But they, like, allowed me to, to be a planner, and we would, like, hook the laptop via HDMI cable up to their screens, and they would have these video teleconferences with all their collaborating units and would share my screen that way.

    22. BF

      It's like a, it's a pile of hacks all put together to-

    23. GD

      [clears throat]

    24. BF

      ... to get you guys into business with these folks.

    25. GD

      And it, it ultimately, like, got us there. In a sense, this was, this was very unimpressive 'cause the revenue numbers were, like, about 15,000 ARR. So we didn't have m- much real revenue. We didn't have any, like, real accreditation to use the software. But we actually got to, um, both an exercise complete and a major real-world con plan, which is basically a, a, a large military plan against a, a big adversary. These are hundreds of pages written entirely in, like, on my computer in the proto version of Onebrief, which was, like, a, a huge feather in our cap.

    26. BF

      Yeah.

    27. GD

      Like, hey, somebody got through a whole con plan in your product.

  13. 15:51 – 17:21

    From prototype credibility to scale: first major contract and JWICS sponsorship

    1. BF

      So now you've got your first customer. You've got some money in your pocket. What was, like, the next big barrier that you guys had to figure out after that point before you could start really going after all these customers and being aggressive on the sales side?

    2. GD

      So we got a verbal on it shortly before YC, and it was signed during.

    3. BF

      Mm-hmm.

    4. GD

      Um, was our first real contract, um, and this was with US Pacific Fleet. And to us, it was a huge contract. It was $322,000, and that was all, like, ARR subscription revenue. We were so proud of it.

    5. BF

      Yeah.

    6. GD

      So the contract actually came with something that was way more important than the money, um, which was they sponsored us onto JWICS, which is the network that the military uses for secret and top secret data. It's basically an intranet. And having, like, a real sponsorship on this was the key to getting our software deployed in places that users could, like, access it and use it and collaborate.

    7. BF

      Mm.

    8. GD

      You know, we wanted, you know, collaborative software that would eventually become the way you run every military staff, and you, you gotta be on your networks to, to do that.

    9. BF

      You get this first deal. You're on the network. What are the next steps then? D- do you go and just start doing a full court press to the other headquarters? Were there a few specific ones that you went after?

    10. GD

      We understood that this was make or break, that we would have no real usage until we were live, that everything we wanted to do was post going live. So we were, like, pretty motivated. There's an art to helping the bureaucracy move fast at something it already wants to do, and I think we, like, availed ourselves of that art.

  14. 17:21 – 19:04

    Operating like a defense software company: the three recurring barriers

    1. BF

      W- was there a moment at which you felt like you'd finally kind of broken through and you, you were in and able to just kind of run this like a more traditional software company and not have all these barriers in front of you?

    2. GD

      Not really. Even today, the major barriers to entry of, um, you know, DOD software, and, like, there's, there's really only three barriers. So if you, if you beat all three, then, then it's just like a commercial business. Um, and the three barriers are facilities clearance, um, authority to operate, and contracting. And they never really go away because, uh, you know, now that we're at, at this certain scale, we, we've, like, pretty, um, grossly exceeded the scale that our original infrastructure was, was intended for.

    3. BF

      Mm.

    4. GD

      And now we're, you know, we're doing another one, and we actually have l- yet another ATO process for, like, our future infrastructure planned after that. Being good at the art of contracting quickly, uh, you know, really helps you in defense. Uh, facilities clearance kind of went away. Once you have it, you have it.

    5. BF

      Right.

    6. GD

      Um, but I, I guess what I mean there is if you know what the three barriers are in defense and you get good at overcoming the barriers, then it's a little closer to a commercial business.

    7. BF

      How did you figure all this stuff out? Like, you didn't know about any of this stuff five years ago, and now you are the expert in it. Like, what- how did you go about learning all this?

    8. GD

      It, it almost helped me not to know how difficult some of those things were going to be because I couldn't be distracted from them. I, I think we were properly focused on just get to product market fit. If we can get a product that every military staff really wants to use, um, we'll be able to figure out the rest.

  15. 19:04 – 24:35

    AI in Onebrief and the long-term vision: automated courses of action

    1. BF

      How, if at all, are you guys today at Onebrief thinking about AI? Are you using it personally to be more productive? Are you guys using it internally? Are you thinking about adding it into the product in some way?

    2. GD

      Inside the product, basically two buckets. Um, bucket one we call the mundane utility bucket, and that's the stuff that's live today. So the goal of the product is make military staffs fast and efficient. If you can get a military command to a, a decision faster, you basically help them win the war. Um, so any little automation of mundane parts of the military operational planning process, I think there's huge numbers of automations available. The second bucket is I think more exciting. Um, so the second bucket is very special military, and the second bucket is about automated course of action. People have been trying really hard for a long time to automate the course of action, which is basically at the meat of a plan, the, like, how do you defend Taiwan? How do you do the specifics of Operation X? And we wanna automate that, and we think we're finally at a point where we can.

    3. BF

      Mm.

    4. GD

      Ultimately, where we wanna get people is c- um, you know, AI-generated course of action that are faster and smarter than any human could come up with.

    5. BF

      You're obviously talking about AI with folks on the other side, with your customers. What, what's your sense of how the military's thinking about AI and using it, like, uh, a- anxieties, excitements? What's your view on how they're thinking about applying this?

    6. GD

      I mean, I think there's a lot more excitement than anxiety. I'm very careful to have every conversation, like, oriented around outcomes and what the product will do for you, and, like, make sure that the value pitch doesn't have the word AI in it. I think that's important because if you get AI in the pitch too early-

    7. BF

      Mm

    8. GD

      ... it becomes, "Look at my cool technology," rather than, "Look at my business outcome." I think the, the military's very excited about AI, but a little bit skeptical of being sold snake oil-

    9. BF

      Yeah

    10. GD

      ... because th- they probably are sold snake oil-

    11. BF

      Yeah

    12. GD

      ... like, pretty, pretty often. So I, I try to, you know, establish trust around the core product, around what we've already accomplished, and then around, like, the uses of AI that are currently live and working and delivering value.

    13. BF

      You've hired dozens, dozens, and dozens of people. You've expanded. You've signed many more contracts. What advice, if any, would you want to give to yourself when you were setting out to do this?

    14. GD

      We could have moved a lot faster if we had known which things were the real bottlenecks.

    15. BF

      Mm.

    16. GD

      So at no time was I working on a thing where I was like, "I don't think this is the most important thing to work on right now." I was just wrong about the, what the most important was. If I'd known that the exercise thing was gonna work, we could have done it with a product that we'd built after one month, and in reality, we did it with a product that we'd built for two years.

    17. BF

      Mm.

    18. GD

      Same for getting on, uh, SIPRNet and JWICS. That one's a little harder because I don't know how, like, my past self would have figured that out without a lot of trial and error. But just knowing this is a really big deal, you're gonna have to find hacky ways to get to it.

    19. BF

      Yep.

    20. GD

      And the sooner you get there, like, there is no product market fit before ATO in the military, so if you don't-

    21. BF

      Mm

    22. GD

      ... work ATO fast enough, you're, you're in trouble.

    23. BF

      What's next for Onebrief?

    24. GD

      Ultimately, where we wanna end up is to be the way that you run a military staff, from battalions up to the joint staff for the, the US and our allies around the world. We wanna make these staffs lightning fast. Something changes in the world, and you know, you, you're able to immediately react. You have an instant plan. We wanna make them require fewer people. I think it's kind of insane to have a headquarters of 1,000 people. I think you should have much smaller headquarters, you know, heavily, you know, armed with the, the right tech tools. To get there, we're, well, investing pretty heavily in core product, um, leveraging a network effect, and use that to get usage to grow quickly, and use that to get everybody to use it.

    25. BF

      So founder motivation is the single biggest determinant of success we've seen here at YC. We can control for all sorts of things, but if a founder is not really in it to win it, it's not gonna happen. Why are you so keyed up and passionate about Onebrief?

    26. GD

      I think what we're doing is on a, on a per dollar basis, the most important thing happening in defense tech in the world. What I mean here is it's very expensive to scale hardware across the military.

    27. BF

      Mm.

    28. GD

      I mean, it solves a real problem. We do need drones, definitely need submarines. But the military is often bottlenecked by decisions. Um, I think that was a huge cause of what happened in the global war on terror. There's a giant gain, like almost a win-the-war level gain in, you know, Taiwan, South China Sea, Korea, Europe, Iran, over having much faster, like superhuman smart military decisions. For one thing, we're, we're doing that, and, uh, for another thing, we think we can do it very, very cheaply, uh, relative to, say, uh, submarines, where once you've built software once, you can scale it to every battalion, every brigade, all the way up to all the joint staffs for allies around the world, and effectively have, you know, one piece of software that drives a- almost every military operational decision worldwide.

    29. BF

      Well, Grant, thank you so much for coming in today and talking about all this with us. It's been great.

    30. GD

      Thanks, Brad. [outro music]

Episode duration: 24:36

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