Chief of Staff

This is a fully remote position, open to applicants in Virginia.

📋 Description

• Act as a strategic and financial advisor to the CEO, facilitating the advancement of company priorities, revenue growth, and operational performance.

• Oversee and enhance Shift5's Revenue Operations function, which includes managing the RevOps team.

• Implement rigor and transparency across pipeline management, bookings, forecasting, conversion rates, revenue performance, and essential commercial metrics.

• Collaborate with the CEO, CFO, and Growth leadership on revenue planning, setting annual targets, forecasts, and compensation strategies.

• Develop and sustain dashboards and reporting systems for pipeline health, revenue performance, and business trends.

• Examine financial and commercial performance to pinpoint risks, opportunities, and areas needing executive intervention.

• Assess the ROI and financial implications of strategic investments, headcount, growth initiatives, and company priorities.

• Create operational rhythms surrounding company KPIs and ensure accountability among leadership.

• Collaborate with Finance, Growth, Product, Mission Delivery, and executive leadership to enhance revenue lifecycle alignment.

• Prepare the CEO for board meetings, financial reviews, strategic planning sessions, and other critical company interactions.

• Convert complex data into straightforward recommendations and decision-making points.

• Direct high-priority strategic initiatives for the CEO, ensuring ownership, execution, and measurable results.

• Foster a high-performing Revenue Operations function and enhance the predictability of pipeline and revenue forecasting.

• Deliver actionable insights into financial and commercial metrics while increasing accountability concerning targets and KPIs.

• Enhance collaboration between Finance, Growth, and other revenue lifecycle teams.

• Detect revenue risks and opportunities promptly to aid swift, data-driven decisions by the CEO.

• Assist Shift5 in scaling with improved financial discipline, revenue predictability, and operational rigor.

⛳️ Requirements

• U.S. citizenship is required due to federal contract stipulations and access to controlled information.

• Strategic, financially-oriented business operator.

• Highly analytical in approach.

• Capable of working across financial analysis, revenue strategy, executive decision-making, and cross-functional execution.

• Experience or capability in Revenue Operations, including managing the RevOps function and direct reports.

• Proficient in analyzing pipeline, bookings, forecasting, conversion, revenue performance, and commercial metrics.

• Skilled in partnering on revenue planning, setting annual targets, forecasts, and compensation planning.

• Competent in building and maintaining dashboards and reporting systems.

• Able to evaluate the ROI and financial impact of strategic investments, headcount, growth initiatives, and company priorities.

• Proficient in translating complex financial, operational, and revenue data into clear recommendations.

• Capable of leading high-priority strategic initiatives and driving measurable results.

🏝️ Benefits

• Competitive base salary.

• Bonus program and equity participation in a rapidly growing startup.

• Employer-covered medical, dental, and vision insurance.

• Health Savings Account with annual contributions from the employer.

• Life insurance coverage.

• Unrestricted paid time off policy.

• Flexible and remote work options.

• Tax-deferred public transit benefits through Metro SmartBenefits (DC/MD/VA).