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.
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