Chief of Staff
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Job Description
Chief of Staff partnering with Shift5’s CEO on revenue operations, forecasting, and financial strategy. Supporting cybersecurity, predictive maintenance, and compliance for defense and commercial fleets.
Responsibilities:
- 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 key commercial metrics
- Partner with the CEO, CFO, and Growth leadership on revenue planning, annual targets, forecasts, and compensation planning
- Build and maintain dashboards and reporting for pipeline health, revenue performance, and business trends
- Analyze financial and commercial performance to identify risks, opportunities, and areas requiring executive action
- Evaluate ROI and financial impact of strategic investments, headcount, growth initiatives, and company priorities
- Establish operating rhythms around company KPIs and leadership accountability
- Partner across Finance, Growth, Product, Mission Delivery, and executive leadership to improve revenue lifecycle alignment
- Prepare the CEO for board meetings, financial reviews, strategic planning sessions, and critical company engagements
- Translate complex data into clear recommendations and decision points
- Lead high-priority strategic initiatives for the CEO and ensure ownership, execution, and measurable outcomes
- Establish a high-performing Revenue Operations function and improve pipeline and revenue forecasting predictability
- Provide actionable visibility into financial and commercial metrics and increase accountability around targets and KPIs
- Improve alignment between Finance, Growth, and other revenue lifecycle teams
- Identify revenue risks and opportunities earlier and support fast, data-driven CEO decisions
- Help Shift5 scale with greater financial discipline, revenue predictability, and operational rigor
Requirements:
- U.S. citizenship required due to federal contract requirements and access to controlled information
- Strategic, financially minded business operator
- Highly analytical
- Ability to work across financial analysis, revenue strategy, executive decision-making, and cross-functional execution
- Experience or capability in Revenue Operations, including managing the RevOps function and a direct report
- Ability to analyze pipeline, bookings, forecasting, conversion, revenue performance, and commercial metrics
- Ability to partner on revenue planning, annual targets, forecasts, and compensation planning
- Ability to build and maintain dashboards and reporting
- Ability to evaluate ROI and financial impact of strategic investments, headcount, growth initiatives, and company priorities
- Ability to translate complex financial, operational, and revenue data into clear recommendations
- Ability to lead high-priority strategic initiatives and drive measurable outcomes
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)
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