Executive Assistant New Rosslyn, VA

Shift5; Virginia; Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Equity in startup

Bonus program

Employer-paid medical, dental and视ion

Health Savings Account with employer 1

Life Insurance

Uncapped paid time off

Transit benefits (Metro SmartBenefits)

Job summary

Shift5 is seeking an Executive Assistant to support the Executive Leadership team. You will manage calendars, coordinate travel, draft communications, and handle confidential information with discretion.

The role requires proactive problem solving, excellent written and verbal communication, and the ability to align schedules with strategic priorities across domestic and international contexts. You will help streamline executive workflows and strengthen cross-functional coordination.

Qualifications

• 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.

Responsibilities

• 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.
• Draft and refine executive correspondence as needed.
• Anticipate scheduling conflicts and oversee domestic and international travel logistics.
• Prepare briefing materials for high-impact meetings.
• Track action items across executive forums including board meetings and offsites.
• Drive process improvements to streamline executive workflows and coordination.
• Maintain systems to track priorities, commitments, and strategic initiatives.

Skills

Calendar management

Travel logistics

Stakeholder coordination

Written communication

Discretion

Cross-functional collaboration

Prioritization

Independence

Tools

Expensify

Monday.com

Google Workspace

Slack

Job description

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
• 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
• 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.