Executive Assistant

About The Company Onebrief is a pioneering collaboration and AI-powered workflow software tailored specifically for military staff. Since its inception in 2019, the company has been dedicated to transforming military operations by enhancing efficiency, speed, and intelligence through innovative technology solutions. Founded by a team of experienced planners, veterans from various military branches, and leading technologists from top-tier software companies, Onebrief has rapidly grown into a global organization. Backed by over $123 million in funding from prominent investors such as Battery Ventures, General Catalyst, Insight Partners, and Human Capital, the company is valued at $1.1 billion. Operating as an all-remote organization, Onebrief maintains a close partnership with military commands worldwide, empowering staff to perform at superhuman levels. The company's culture emphasizes ownership, excellence, and a collaborative spirit akin to an Olympic team, striving to make a meaningful impact where it matters most. About The Role We are seeking a highly organized, proactive, and strategic Executive Assistant to support our Chief Information Officer (CIO). This role extends beyond traditional administrative tasks, serving as a trusted partner in managing the CIO’s operational and strategic priorities. The successful candidate will be responsible for coordinating the CIO’s calendar, maintaining visibility across key initiatives, and creating a structured environment that ensures organizational alignment and momentum. This position involves developing a deep understanding of business objectives, challenges, and opportunities, enabling the individual to facilitate decision-making processes and information flow efficiently. The role requires a blend of operational excellence, strategic thinking, and executive enablement, contributing significantly to the success of a fast-growing, high-stakes technical organization. Qualifications

• 37+ years of experience supporting senior technical leaders as an Executive Assistant, Chief of Staff, Program Coordinator, or in Operations roles, preferably in high-complexity environments
• Exceptional written and verbal communication skills, with the ability to translate complex information into clear, actionable summaries
• Strong operational instincts including organization, prioritization, and project tracking
• Proficiency with tools such as Slack, Notion, Google Workspace, and project dashboards
• High level of ownership, anticipation, and proactive partnership
• Discretion, integrity, and professionalism in handling sensitive information
• Willingness to travel approximately 20-25%
• Must be based in the US Central Time Zone

Responsibilities

• Own and manage the CIO’s calendar and operating rhythm, ensuring meetings are purposeful, protected time for deep work is scheduled, and weekly/monthly cadences are maintained
• Manage communication channels including Slack, Notion, and email by drafting updates, summarizing meetings, and capturing decisions and next steps
• Maintain and update the CIO’s project dashboard, tracking milestones, risks, owners, and follow-through on multiple cross-functional initiatives
• Serve as a coordination hub and proxy for the CIO by aligning stakeholders, managing vendor and partner interactions, and ensuring expectations and timelines are clear
• Develop and sustain operational structures such as weekly CIO syncs, daily briefs, board/investor preparations, compliance reviews, and ongoing initiative updates
• Facilitate effective information flow and decision-making processes across the organization
• Anticipate needs and proactively address potential issues before they arise
• Support strategic initiatives and special projects as assigned

Benefits

• Competitive salary and comprehensive benefits package
• Flexible remote work environment
• Opportunities for professional growth and development within a rapidly expanding organization
• Collaborative and innovative work culture
• Travel opportunities (20-25%) for on-site engagements
• Health, dental, and vision insurance options
• Paid time off and holidays

Equal Opportunity Onebrief is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, gender identity or expression, age, disability, or veteran status. We encourage all qualified individuals to apply and join our mission to revolutionize military operations through innovative technology solutions.