Executive Assistant

About Shift5Shift5 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 DoManage complex calendars, prioritize engagements, and coordinate internal and external stakeholders across the executive teamHandle sensitive and confidential information with discretion and sound judgmentCoordinate, set up, and prepare for onsite engagements, executive visits, and high-profile meetingsManage expense reporting and reconciliation with accuracy and timelinessServe as a trusted point of contact for internal and external communications, drafting and refining executive correspondence as neededProactively anticipate scheduling conflicts, resolve constraints, and oversee domestic and international travel logisticsPrepare briefing materials and ensure leaders are fully equipped for high-impact meetingsTrack action items and follow-ups across executive forums, including board meetings and leadership offsitesDrive process improvements that streamline executive workflows, enhance organization, and strengthen cross-functional coordinationMaintain structured systems to track priorities, commitments, and strategic initiativesWhat Success Looks LikeExecutives operate with clarity and minimal administrative frictionCalendars are optimized around strategic prioritiesKey meetings are well-prepared and well-documentedLeadership communication flows smoothly across teamsOperational discipline improves across the executive functionWhat We're Looking For5+ years of experience supporting C-level or senior executive leadersExperience supporting multiple executives simultaneouslyProficiency in Expensify, Monday.com, and modern collaboration tools (Google Workspace, Slack, etc.)Strong organizational and prioritization skills in high-growth environmentsExceptional written and verbal communication skillsHigh level of discretion and professional judgmentAbility to operate independently and anticipate needsExperience with Google Workspace, Slack, calendar management tools, and collaboration platformsExperience in defense-tech, SaaS, or high-growth startup environments preferredCompensation & BenefitsCompensation & Benefits:Base Salary: $90,000-$120,000Bonus program and equity in a fast-growing startupCompetitive salary and stock options in a fast-growing startupEmployer-paid medical, dental and vision coverageHealth Savings Account with annual employer contributionsLife InsuranceUncapped paid time off policyFlexible work & remote work policyTax-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.Privacy Policy and Notice for Shift5, Inc. Job Applicants, Employees & Contractors