---
title: 'Executive Assistant at Shift5'
canonical: 'https://feeny.ai/job/executive-assistant-shift5-rosslyn-103wwb3j656d'
type: 'job'
last_seen: '2026-10-13'
---

# Executive Assistant at Shift5

- **Company:** Shift5
- **Location:** Rosslyn, VA
- **Work type:** remote
- **Posted:** 2026-10-12
- **Last confirmed live:** 2026-10-13
- **Apply:** https://job-boards.greenhouse.io/shift5/jobs/6222747004

## Job description

## 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.

[Privacy Policy and Notice for Shift5, Inc. Job Applicants, Employees & Contractors](https://docs.google.com/document/d/e/2PACX-1vSoqk1SJimaI-_eN6ivV05XJKDJIvh7t32xMVM_7CEFDjGHGjEyFAs6_4v7Uv_OxALOz8g_IzQ6VYmn/pub)

## About Shift5

## Company Overview
- **One-liner**: Shift5 provides an operational intelligence platform that analyzes onboard serial bus and radio frequency data from military and commercial fleets to deliver near real-time threat detection, predictive maintenance, and compliance automation.
- **Entity Type**: Private – Series C (raised $75M ~10 months ago; total funding $180.75–$185M)
- **Headquarters**: Arlington, Virginia, USA
- **Founded**: 2019
- **Founders**: Josh Lospinoso (co-founder, now Board Member); the company was also founded by former U.S. Army Cyber Command officers.

## Core Business
- **Primary industries**: Defense, aviation, ground vehicles, maritime, rail – operational technology (OT) cybersecurity and observability.
- **Target customers**: B2B – U.S. Department of Defense, military branches (Air Force, Army), commercial airlines, rail operators, and critical infrastructure fleet managers.
- **Mission / purpose**: “We exist to protect the servicemembers who defend our nation and secure the critical systems that keep our economy moving.”

## Products & Services
- **Shift5 Operational Intelligence Platform**: SaaS/software that ingests serial bus and RF data from fleets (aircraft, ground vehicles, ships, trains) to detect faults, cyber threats, and GPS spoofing in near real-time.
- **Predictive Maintenance**: Transforms serial bus data into proactive maintenance insights to reduce unplanned downtime and improve mission readiness.
- **Cybersecurity / EW**: Analyzes serial bus traffic and RF data to flag threats (e.g., GPS spoofing, advanced persistent threats) and enable operator action.
- **Fleet Compliance**: Processes security log files from commercial aircraft to verify compliance with aviation regulations and identify security incidents.
- **RF-Enabled GPS Threat Detection**: Plug-and-play capability that provides early warning of GPS spoofing up to 200 nautical miles away.
- **Research Services**: Expert-led security assessments, novel threat research, and specialized tooling for protecting critical assets.

## Market Standing
- **Valuation / Market Cap**: Not disclosed (private company).
- **Key Metric**: Total venture capital funding – **$180.75M** (CB Insights) or **$185M** (company site) across multiple rounds; last raise was a **$75M Series C** approximately 10 months prior to the search date.
- **Notable Investors / Partners**: Partners include **Boeing** (joint fault/threat detection initiative), **Anduril** (next-generation command & control for Army), **Rune Technologies** (defense platform sustainment), **L3Harris** (Toby Magsig, former L3Harris executive, now President & CEO). Federal contracts include **U.S. Air Force F-16** upgrades, **CSfC listing** for classified operations.
- **Growth Signals**:
  - Over **100 full-time employees** across five time zones.
  - Formalized executive leadership team (Toby Magsig confirmed CEO, new C-Suite roles) following “best Q1 in company history.”
  - Launched advanced RF-enabled GPS threat detection (Jan 2026).
  - Achieved **Commercial Solutions for Classified (CSfC)** listing (June 2026).
  - Selected for next-gen F-16 upgrades (Dec 2025).
  - Partnerships with Anduril, Boeing, and Rune Technologies.

## Competitive Advantages
- **Unique data access**: Only platform extracting and analyzing raw serial bus (MIL-STD-1553, ARINC 429) and RF data from military/commercial fleets, often in contested environments.
- **Early-warning GPS spoofing detection**: RF-based method that detects threats up to 200 nautical miles away – a capability few competitors offer.
- **Deep defense heritage**: Founders and leadership with U.S. Army Cyber Command and L3Harris backgrounds; strong trust within DoD and prime contractors.
- **Regulatory compliance**: NIAP and CSfC listings enable broader use in classified and sensitive operations.
- **Partnerships with primes**: Boeing, Anduril, L3Harris – validated integration into major platforms.

## Strategic Focus
- **Acceleration across defense and critical infrastructure** – expanding beyond aviation into ground vehicles, maritime, and rail.
- **Product expansion**: Continued investment in RF-based detection, predictive maintenance, and integration with partner ecosystems (e.g., Lattice Mesh).
- **Talent scaling**: Hiring across deployment strategy, field engineering, hardware/software engineering, and go-to-market roles.
- **Executive leadership stability**: Formalized C-suite to support growth and market penetration.

## Why Work Here
- **Culture**: “Low-ego, high-horsepower” team from diverse backgrounds (public/private sectors). Values include Mission-First Mindset, Relentless Innovation, and Data-Driven Precision.
- **Work model**: Many roles are “Remote/HQ” – flexibility to work remotely while maintaining an HQ in Arlington, VA. Open positions include Deployment Strategist, Field Engineer, Hardware Engineer, Systems Integration Engineer, and Proposal Manager.
- **Benefits**:
  - Comprehensive medical coverage with HSA contributions.
  - **12 weeks paid parental leave** (birth or adoption).
  - **Unlimited time off** plus paid holidays.
  - 401(k) plan (pre-tax and Roth options via Vanguard).
  - Financial and legal support through internal team.
- **Engineering culture**: Focus on solving tough OT problems; hardware and software teams work closely; emphasis on scalability and real-time data.
- **Impact**: Direct contribution to protecting service members and critical national infrastructure.

## Sources
1. [shift5.io – Homepage](https://shift5.io/)
2. [shift5.io – Company page](https://shift5.io/company/)
3. [shift5.io – Careers page](https://shift5.io/careers/)
4. [CB Insights – Shift5 profile](https://www.cbinsights.com/company/shift5)
5. [LinkedIn – Shift5](https://www.linkedin.com/company/shift5)

## Other roles at Shift5

- [Principal Platform Engineer](https://feeny.ai/job/principal-platform-engineer-shift5-rosslyn-va-0n5k1nczhwb2) — Rosslyn VA, OR
- [Senior Buyer & Strategic Sourcing Specialist](https://feeny.ai/job/senior-buyer-strategic-sourcing-specialist-shift5-rosslyn-jqq8hqd3n8mh) — Rosslyn, VA
- [Mission Operations Specialist - San Diego](https://feeny.ai/job/mission-operations-specialist-san-diego-shift5-remote-qm3y8dy6pyzm)
- [Mission Operations Specialist - Fort Carson](https://feeny.ai/job/mission-operations-specialist-fort-carson-shift5-remote-w76nc1mn6y0h)
- [Mission Operations Specialist - Fort Hood](https://feeny.ai/job/mission-operations-specialist-fort-hood-shift5-remote-wa679c5y52xf)
- [Mechanical Engineer](https://feeny.ai/job/mechanical-engineer-shift5-rosslyn-nj10177tpk3j) — Rosslyn, VA
- [Test Engineer](https://feeny.ai/job/test-engineer-shift5-rosslyn-c67hm7s3g91p) — Rosslyn, VA
- [People & Talent Coordinator](https://feeny.ai/job/people-talent-coordinator-shift5-rosslyn-whakwvyytmwc) — Rosslyn, VA
- [Systems Engineer](https://feeny.ai/job/systems-engineer-shift5-rosslyn-va-4getq5a9cfvb) — Rosslyn VA, OR
- [Senior Quality and Process Engineer](https://feeny.ai/job/senior-quality-and-process-engineer-shift5-rosslyn-kn7pf1azpbht) — Rosslyn, VA