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Chief of Staff

Rosslyn, VA or Remote

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.

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