---
title: 'Chief of Staff at Shift5'
canonical: 'https://feeny.ai/job/chief-of-staff-shift5-rosslyn-va-sz807dkp3964'
type: 'job'
last_seen: '2026-09-22'
---

# Chief of Staff at Shift5

- **Company:** Shift5
- **Location:** Rosslyn VA, OR
- **Work type:** remote
- **Posted:** 2026-09-19
- **Last confirmed live:** 2026-09-22
- **Apply:** https://job-boards.greenhouse.io/shift5/jobs/6201796004

## 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 strategic, financially minded Chief of Staff to partner directly with the CEO and help drive Shift5's growth, revenue performance, and operating strategy.

Reporting directly to the CEO, this role will sit at the intersection of executive leadership, Finance, Growth, and Revenue Operations. The Chief of Staff will help translate company strategy into measurable business outcomes, bring greater rigor to revenue forecasting and operating performance, and ensure the CEO and executive team have the data and insights needed to make informed decisions.

This role will also have significant ownership of Revenue Operations, including managing the RevOps function and a direct report supporting revenue operations. This person will be responsible for creating greater visibility, predictability, and accountability across Shift5's revenue engine.

This is not a traditional administrative Chief of Staff role. The ideal candidate is a highly analytical business operator who can move seamlessly between financial analysis, revenue strategy, executive decision-making, and cross-functional execution.

Note: This position requires U.S. citizenship due to federal contract requirements and access to controlled information.

## What You'll Do

- Serve as a strategic and financial thought partner to the CEO, helping drive company priorities, revenue growth, and operating performance.
- Own and develop Shift5's Revenue Operations function, including management of the RevOps team.
- Drive rigor and visibility across pipeline, bookings, forecasting, conversion, revenue performance, and other key commercial metrics.
- Partner closely with the CEO, CFO, and Growth leadership on revenue planning, annual targets, forecasts, and compensation planning.
- Build and maintain dashboards and reporting that provide leadership with a clear view of pipeline health, revenue performance, and business trends.
- Analyze financial and commercial performance to identify risks, opportunities, and areas requiring executive action.
- Evaluate the ROI and financial impact of strategic investments, headcount, growth initiatives, and other company priorities.
- Establish operating rhythms around company KPIs and ensure leadership has clear accountability against business and revenue objectives.
- Partner across Finance, Growth, Product, Mission Delivery, and executive leadership to improve alignment across the revenue lifecycle.
- Prepare the CEO for board meetings, financial reviews, strategic planning sessions, and other critical company engagements.
- Translate complex financial, operational, and revenue data into clear recommendations and decision points.
- Lead high-priority strategic initiatives on behalf of the CEO and ensure decisions translate into clear ownership, execution, and measurable outcomes.

What Success Looks Like

- Become a trusted strategic and financial advisor to the CEO and executive leadership team.
- Establish a high-performing Revenue Operations function with clear ownership and accountability.
- Improve the accuracy and predictability of pipeline and revenue forecasting.
- Give leadership consistent, actionable visibility into the company's most important financial and commercial metrics.
- Create greater accountability around revenue targets, company KPIs, and strategic priorities.
- Improve alignment between Finance, Growth, and other teams involved in the revenue lifecycle.
- Identify revenue risks and opportunities earlier and translate those insights into action.
- Improve the CEO's ability to make fast, data-driven decisions and focus his time on the company's highest-impact priorities.
- Help Shift5 scale with greater financial discipline, revenue predictability, and operational rigor.

## Compensation & Benefits

- Competitive base salary
- Bonus program and equity 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)

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