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 senior leadership team, including the SVP of Growth Officer, CTO, President & Interim CEO, Chief Legal Officer, VP of Product Strategy & Partnerships, and VP of Finance.

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: $90,000-$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)

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.

We are committed to building an inclusive culture of belonging that embraces the diversity of our people and represents the communities in which we work and the customers we serve. We know the happiest and highest performing teams include people with diverse perspectives and ways of solving problems. We strive to attract and retain talent from all backgrounds and create workplaces where everyone feels empowered to bring their full, authentic selves to work.

Shift5 is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sexual orientation, gender identify, national origin, disability, age, marital status, ancestry, projected veteran status, or any other protected group or class.