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Shift5

Chief of Staff

Shift5

. Serve as a strategic and financial thought partner to the CEO, helping drive company priorities, revenue growth, and operating performance .

Posted 9/19/2026full-timeRemote • Virginia • United StatesLeadWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in Revenue Operations, financial analysis, and strategic planning, with a strong ability to translate complex data into actionable insights. Proven track record in managing teams, driving revenue growth, and improving operational performance through effective collaboration across functions.

Highest-signal resume keywords
Revenue Operations ManagementFinancial AnalysisStrategic PlanningDashboard DevelopmentCross-Functional Collaboration

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Revenue StrategyForecastingPipeline AnalysisCommercial MetricsROI EvaluationData AnalysisKPI ManagementPerformance MetricsRevenue Growth InitiativesOperational Rigor
Soft Skills
Analytical ThinkingStrategic MindsetDecision-MakingLeadershipCommunication
Industry Keywords
Revenue LifecycleFinancial DisciplineExecutive EngagementPerformance AccountabilityBusiness Trends

About the role

Key responsibilities & impact
  • 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

What you’ll need
  • 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

Comp & perks
  • 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)