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during the 2014 Ebola crisis when he realized something: the military’s most critical decisions were being made with outdated tools and slow, legacy workflows.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

EPISODE INFO

Released: May 13, 2025
Duration: 24m
Channel: YC Root Access
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

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during the 2014 Ebola crisis when he realized something: the military’s most critical decisions were being made with outdated tools and slow, legacy workflows.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

SPEAKERS

Brad Flora
host
Host of YC Root Access who interviews startup founders about their companies and go-to-market strategies.
Grant Demaree
guest
Former US Army officer and co-founder of Onebrief (YC Summer ’21), building software for military operational planning.

EPISODE SUMMARY

In this episode of YC Root Access, featuring Brad Flora and Grant Demaree, How Onebrief Is Fixing Military Planning With Software explores onebrief modernizes military planning, navigating procurement, security, and adoption barriers Onebrief turns operational military planning from email-and-slide-deck chaos into a shared, structured system where plan components update everywhere automatically.

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