YC Root Access

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during the 2014 Ebola crisis when he realized something: the military’s most critical decisions were being made with outdated tools and slow, legacy workflows.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

BFBrad FlorahostGDGrant Demareeguest

May 13, 2025·24m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Onebrief’s mission: speeding up operational military planning

   Grant Demaree explains that Onebrief builds software for operational military planning—the process behind most decisions made by military headquarters, from battalions to combatant commands. The core thesis is that making planning faster and smarter has outsized impact on military effectiveness.

2. 2

   Company scale and traction: adoption, growth rates, team, and valuation

   Grant shares Onebrief’s current growth and company scale to contextualize how broadly the product is being adopted. He highlights rapid quarter-over-quarter usage growth and the company’s fundraising milestone.

3. 3

   The old way: Word/PowerPoint, emailed slide decks, and slow ops orders

   The discussion contrasts Onebrief with the legacy workflow, which is dominated by Word and PowerPoint despite many attempted replacements. Planning often means hundreds of slides, constant emailing across many units, and producing large written orders.

4. 4

   How Onebrief works: cards, reusable data, and synced outputs

   Grant explains the product’s user experience: a modular, card-based system that creates multiple planning outputs from the same underlying data. Changes propagate everywhere—documents, matrices, maps—reducing rework and enabling faster iteration.

5. 5

   Compression story: rewriting a major course of action in three hours

   A concrete example illustrates the time savings: when leadership rejected a proposed course of action, planners rebuilt the plan rapidly using Onebrief. What typically takes weeks was completed in hours, including updated visuals and written products.

6. 6

   Origin story: spotting the planning bottleneck in Liberia and Iraq

   Grant traces the idea to his Army experience—first during the Ebola response in Liberia, then later at CJTF-OIR in Baghdad. Seeing repeated inefficiencies convinced him the planning process was a systemic bottleneck worth fixing.

7. 7

   Selling to “the military” isn’t one sale: navigate commands and budgets

   Grant reframes DOD as many semi-independent organizations with their own budgets rather than a single monolith. This enables early founders to sell to the specific command with the strongest need and closest proximity to end users.

8. 8

   Early contracting hack: the government purchase card entry point

   The first sale required convincing just one person by using a government purchase card (a credit-card-like procurement tool). This bypassed long contracting cycles and enabled Onebrief to get into headquarters and learn from real users.

9. 9

   Early product discovery mistakes and correction: build vs. interview

   Grant admits they initially started building too quickly (even prototyping in MATLAB) before validating needs. They then corrected by conducting extensive stakeholder interviews to understand operational planning requirements deeply.

10. 10

    Finding users without access: paid Saturday planning exercises

    Because they couldn’t access real headquarters initially, the team created intensive, paid scenario exercises by recruiting planners via cold LinkedIn outreach. They ran side-by-side comparisons: Word/PowerPoint vs. early Onebrief, observing workflows and iterating fast.

11. 11

    First champion and embed strategy: winning trust at Pacific Fleet

    A warm intro led to Captain Dave Fields at US Pacific Fleet, who had seen many failed attempts. Grant’s candid approach and request to embed for months (rather than asking for money) built trust and opened the door to real-world trials.

12. 12

    Security and deployment reality: ATO, SCIF constraints, and “one-laptop” workaround

    Grant explains the practical barriers to deploying defense software, especially for classified environments requiring Authority to Operate (ATO). Before they were ready for full accreditation, they used a hack: a single locked-down laptop brought into a SCIF, with strict constraints and disposal rules.

13. 13

    From proto-usage to real contract: JWICS sponsorship and scaling distribution

    The first major contract (signed during YC) mattered not just for ARR, but because it enabled network sponsorship onto JWICS for secret/top secret collaboration. That sponsorship unlocked broader deployment and made the product usable as true collaborative software.

14. 14

    Enduring barriers and the AI roadmap: utilities now, automated courses of action next

    Grant outlines the three persistent defense software barriers—facilities clearance, ATO, and contracting—and notes they don’t fully disappear as the company scales. He then describes Onebrief’s AI strategy: near-term mundane automation and a longer-term push toward AI-generated courses of action that beat human planning speed and quality.

15. 15

    Founder lessons, future vision, and why the mission matters

    Grant reflects that progress would have been faster with clearer understanding of true bottlenecks (exercises, ATO/JWICS access). He closes with a vision of Onebrief as the operating system for military staffs worldwide—smaller, faster headquarters making better decisions—and explains why software can be an unusually cost-effective lever in defense compared to hardware.