YC Root AccessHow Onebrief Is Fixing Military Planning With Software
CHAPTERS
- 0:00 – 1:09
Onebrief’s mission: speeding up operational military planning
Grant Demaree explains that Onebrief builds software to make operational planning faster and smarter across military headquarters. The core idea is that accelerating planning accelerates decisions, which can materially affect outcomes in conflict and crisis response.
- •Operational planning underpins most military decisions at every echelon
- •Improving planning speed and quality has outsized strategic impact
- •Onebrief positions software as a leverage point versus expensive hardware
- •Focus on cross-command collaboration and decision advantage
- 1:09 – 1:46
Company traction and scale: adoption, headcount, and Series C
Brad asks for perspective on how far Onebrief has grown. Grant shares usage growth, team size, and valuation, emphasizing broad adoption across military headquarters.
- •Software used in many headquarters worldwide
- •Usage growing ~2.75x quarter over quarter (~57x YoY)
- •Team size around 144 people
- •Series C raised at ~$650M valuation
- 1:46 – 2:21
The legacy workflow: Word, PowerPoint, and emailed slide decks
Grant describes how military planning is still largely done with Word documents and massive PowerPoint decks. Despite many prior attempts to replace this workflow, the incumbents remain sticky and collaboration is painful and slow.
- •Plans often involve hundreds of slides and many contributors
- •Artifacts are emailed between units and commands, creating version chaos
- •Outputs include operations orders and base plans
- •Many prior tools tried (and failed) to displace Office workflows
- 2:21 – 3:24
How Onebrief works: cards, shared data, and multi-output planning
Grant outlines Onebrief’s product design: reusable “cards” representing facts, units, and tasks that feed every output. Updating a single building block propagates across documents, maps, and matrices, reducing rework on complex plans.
- •Card-based data model for reusable planning components
- •Outputs include sync matrices, operations orders, slides, and maps
- •Single-source-of-truth updates automatically across artifacts
- •Targets the slowest, largest plans (e.g., O-plans) that can take years
- 3:24 – 4:06
Compression in practice: rewriting a major course of action in hours
A concrete story illustrates the value: a senior leader rejects a course of action, which would normally cause weeks of rework. Using Onebrief, planners regenerate the full set of deliverables—maps, matrices, written plan, and slides—in three hours.
- •Rapid iteration after leadership feedback
- •Coordinated updates across multiple planning artifacts
- •Hours instead of weeks for end-to-end replanning
- •Demonstrates the leverage of linked planning components
- 4:06 – 5:38
Origin story: seeing planning dysfunction during Ebola and OIR
Grant traces the idea back to his time as a young Army officer observing headquarters planning during the 2014 Ebola response in Liberia. Later, at CJTF-OIR in Baghdad, he recognized the inefficiency as systemic and decided to leave the Army to fix it.
- •Fresh-eye exposure to HQ planning during Ebola response
- •Noticed delays and inefficiencies caused by manual workflows
- •Confirmed pattern at CJTF-OIR (Iraq/Syria against ISIS)
- •Motivation: improve the decision engine that drives operations
- 5:38 – 6:52
Understanding the customer: selling to many commands, not one monolith
Brad and Grant unpack a key go-to-market insight: the military is not a single buyer, but many budget-owning organizations. That structure allows startups to start with the command that needs the product most rather than tackling DoD-wide procurement first.
- •Defense organizations are fragmented with independent budgets
- •~1,200 US commands are potential buyers/users for Onebrief
- •Start with the most acute pain point to move faster
- •Staying close to end users improves iteration and adoption
- 6:52 – 8:31
Early sales hack: government purchase cards to bypass procurement drag
Grant explains how the first deal could be as small as one decision-maker using a government purchase card, avoiding long contracting cycles. The goal early wasn’t revenue scale—it was access to real users and real workflows inside a headquarters.
- •Initial sale involved a single buyer/advocate
- •Government purchase cards enable quick purchases (often up to ~$25K)
- •Short-circuits complex contracting for early validation
- •Primary value: physical access to users and environment
- 8:31 – 9:14
Early product misstep and correction: build less, interview more
Grant admits they initially started building too soon, even prototyping in MATLAB, which helped recruit a strong co-founder but delayed learning. They then conducted ~200 interviews across stakeholders in operational planning to properly understand needs.
- •Started with clickable mockups and an early MATLAB prototype
- •Prototyping signaled seriousness and attracted talent
- •~200 stakeholder interviews reshaped understanding of requirements
- •Lesson: structured discovery was essential, not optional
- 9:14 – 10:45
Getting real feedback without access: Saturday planning exercises
With limited access to real headquarters, Onebrief staged all-day exercises by recruiting planners via cold LinkedIn outreach. Teams solved the same scenario using Office vs. the Onebrief prototype, generating direct observational feedback and strong advocacy.
- •Cold outreach to majors–colonels to participate in paid exercises
- •Designed robust scenarios to simulate real planning pressure
- •A/B comparison: Word/PowerPoint vs. proto Onebrief workflows
- •Exercises produced enthusiasm and warm introductions into commands
- 10:45 – 12:35
First real foothold: embedding at Pacific Fleet via a warm intro
A warm introduction to Captain Dave Fields at US Pacific Fleet became the turning point. Grant built trust through candid discovery, then asked to embed for months and start with a nominal purchase-card transaction—an “earnest” ask focused on execution.
- •Prospect had evaluated ~10 failed prior solutions
- •Two-hour discovery call helped establish credibility and trust
- •Asked to embed for three months to work on real plans
- •Small initial payment used as a mechanism to get inside
- 12:35 – 15:51
Security and deployment barriers: ATO, SCIF access, and “one-laptop” hacks
Grant explains the “authority to operate” (ATO) problem: without accreditation, software can’t run on classified networks. To avoid years of bureaucracy too early, they deployed on a single laptop (Grant’s), brought into a SCIF under strict constraints, and used screen sharing to participate in planning.
- •ATO is required to run software on military networks, especially classified
- •ATO can take years and cost millions if done poorly
- •Workaround: single laptop with Wi‑Fi/Bluetooth disabled; device surrendered for destruction
- •Enabled real plan contribution despite non-collaborative, offline constraints
- 15:51 – 17:21
From prototype credibility to scale: first major contract and JWICS sponsorship
The first major contract—$322K ARR with Pacific Fleet—mattered less for revenue than for access. Sponsorship onto JWICS (secret/top secret intranet) unlocked deployability and collaboration, enabling real usage and future expansion.
- •First substantial subscription contract signed around YC timeframe
- •JWICS sponsorship enabled broader deployment for classified collaboration
- •Network access was prerequisite for true product-market fit
- •Shifted from demo hacks to scalable operational usage
- 17:21 – 19:04
Operating like a defense software company: the three recurring barriers
Grant frames defense software success around clearing three ongoing hurdles: facilities clearance, authority to operate, and contracting. These challenges persist even at scale as infrastructure and accreditation must evolve, but mastering them makes the business feel more like commercial SaaS.
- •Three core barriers: facilities clearance, ATO, and contracting
- •Facilities clearance is mostly one-and-done; others recur with scale
- •ATO must be revisited as infrastructure and scope expand
- •Speed comes from learning how to move bureaucracy on what it already wants
- 19:04 – 24:36
AI in Onebrief and the long-term vision: automated courses of action
Grant describes two AI tracks: practical automations already live, and the more ambitious goal of generating courses of action that surpass human planning. He also notes the military’s excitement paired with skepticism, so he sells outcomes first and avoids leading with “AI.”
- •AI bucket 1: mundane utility automations to speed staff work
- •AI bucket 2: automated course-of-action generation (hard, high value)
- •Positioning: emphasize outcomes over “cool AI” to build trust
- •Vision: faster, smaller staffs with instant, high-quality plans at scale
