Executive Assistant

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.

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

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

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

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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