Executive Assistant, Office of the CIO

Onebrief is collaboration and AI-powered workflow software designed specifically for military staffs. By transforming this work, Onebrief makes the staff as a whole superhuman - meaning faster, smarter, and more efficient.

We take ownership, seek excellence, and play to win with the seriousness and camaraderie of an Olympic team. Onebrief operates as an all-remote company, though many of our employees work alongside our customers at military commands around the world.

Founded in 2019 by a group of experienced planners, today, Onebrief’s team spans veterans from all forces and global organizations, and technologists from leading-edge software companies. We’ve raised $320m+ from top-tier investors, including Battery Ventures, General Catalyst, Sapphire Ventures, Insight Partners, and Human Capital, and today, Onebrief is valued at $2.15B. With this continued growth, Onebrief is able to make an impact where it matters most.

We’re looking for a highly organized, proactive, and trusted Executive Assistant to partner with our CIO. This role is a blend of strategic coordination, operational excellence, and executive enablement. You’ll manage the CIO’s operating rhythm, maintain visibility across key initiatives, and create structure that keeps the organization aligned and moving efficiently.

This is not traditional administrative support. This is a high-touch and strategic role in which you’ll develop a deep understanding of business priorities, challenges, and opportunities, and ensure our CIO has the relevant information at the right time. You will help shape how decisions are made, how information flows, and how we maintain momentum across a fast-growing, high-stakes technical organization.

You’re someone who thrives on creating order, clarity, and forward motion. You anticipate needs before they surface, connect dots across conversations and projects, and bring a calm, thoughtful presence to complex situations. You pride yourself on turning complexity into clear next steps, and you’re comfortable acting as an executive proxy with internal leaders, vendors, and partners.

You work best when embedded in close partnership with a senior leader — building trust through reliability, discretion, excellent communication, and strong judgment. You enjoy documenting decisions, structuring information, and ensuring nothing slips through the cracks. You’re energized by creating the operating environment that allows a technical leader to focus on the highest-impact work.

• Own the CIO’s calendar and operating rhythm, ensuring meetings have clear purpose, deep-work time is protected, and weekly/monthly cadences run smoothly.

• Manage communication and context across Slack, Notion, and email, drafting updates, summarizing meetings, and ensuring decisions and next steps are captured clearly.

• Maintain the CIO’s project dashboard, tracking milestones, risks, owners, and follow-through across multiple cross-functional initiatives.

• Act as a coordination hub and CIO proxy, aligning stakeholders, managing vendor and partner interactions, and ensuring expectations and timelines remain clear.

• Create and maintain operational structure, including weekly CIO syncs, daily briefs, board/investor prep, compliance reviews, and ongoing initiative updates.

• 3–7+ years in an Executive Assistant, Chief of Staff, Program Coordinator, or Operations role supporting a senior technical leader (or equivalent experience in a high-complexity environment).

• Exceptional written and verbal communication, especially in translating complex details into concise, actionable summaries.

• Strong operational instincts: organization, prioritization, project tracking, and an ability to proactively identify gaps and blockers.

• High comfort working in tools like Slack, Notion, and Google Workspace; experience maintaining project dashboards or documentation systems.

• A mindset of ownership, anticipation, and partnership; someone who sees around corners and stays one step ahead.

• High integrity, discretion, and professionalism when handling sensitive information.

• Willingness and ability to travel 20-25%.

• Must be based in US Central Time.

• Experience working in defense technology, cybersecurity, or related industries

Notice to Third Party Recruitment Agencies
Please note that Onebrief does not accept unsolicited resumes from recruiters or employment agencies. In the absence of an executed Recruitment Services Agreement, there will be no obligation to any referral compensation or recruiter fee. In the event a recruiter or agency submits a resume or candidate without an agreement Onebrief explicitly reserves the right to pursue and hire those candidate(s) without any financial obligation to the recruiter or agency. Any unsolicited resumes, including those submitted to hiring managers, shall be deemed the property of Onebrief.