Executive Assistant

About Shift5 Shift5 is building the data platform for onboard operational technology (OT). We deliver cybersecurity, predictive maintenance, and compliance capabilities that enable defense and commercial fleets to operate with greater readiness, resilience, and mission assurance. We are seeking a mission-aligned Executive Assistant to support our Executive Leadership team. What You’ll Do • Manage complex calendars, prioritize engagements, and coordinate internal and external stakeholders across the executive team • Handle sensitive and confidential information with discretion and sound judgment • Coordinate, set up, and prepare for onsite engagements, executive visits, and high-profile meetings • Manage expense reporting and reconciliation with accuracy and timeliness • Serve as a trusted point of contact for internal and external communications, drafting and refining executive correspondence as needed • Proactively anticipate scheduling conflicts, resolve constraints, and oversee domestic and international travel logistics • Prepare briefing materials and ensure leaders are fully equipped for high-impact meetings • Track action items and follow-ups across executive forums, including board meetings and leadership offsites • Drive process improvements that streamline executive workflows, enhance organization, and strengthen cross-functional coordination • Maintain structured systems to track priorities, commitments, and strategic initiatives What Success Looks Like • Executives operate with clarity and minimal administrative friction • Calendars are optimized around strategic priorities • Key meetings are well-prepared and well-documented • Leadership communication flows smoothly across teams • Operational discipline improves across the executive function What We’re Looking For • 5+ years of experience supporting C-level or senior executive leaders • Experience supporting multiple executives simultaneously • Proficiency in Expensify, Monday.com, and modern collaboration tools (Google Workspace, Slack, etc.) • Strong organizational and prioritization skills in high-growth environments • Exceptional written and verbal communication skills • High level of discretion and professional judgment • Ability to operate independently and anticipate needs • Experience with Google Workspace, Slack, calendar management tools, and collaboration platforms • Experience in defense-tech, SaaS, or high-growth startup environments preferred Compensation & Benefits Compensation & Benefits: • Base Salary: $85,000 - $120,000 • Bonus program and equity in a fast-growing startup • Competitive salary and stock options in a fast-growing startup • Employer-paid medical, dental and vision coverage • Health Savings Account with annual employer contributions • Life Insurance • Uncapped paid time off policy • Flexible work & remote work policy • Tax-deferred public transit benefits with Metro SmartBenefits (DC/MD/VA) Equal Opportunity Employer Shift5 is committed to equal employment opportunity and affirmative action. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or other protected characteristics. Privacy Policy and Notice for Shift5, Inc. Job Applicants, Employees & Contractors