Chief of Staff

Location: Based in the Eastern Time Zone. Remote with 25% travel. 

Reports To: CEO

Summary

We are looking for a highly analytical, organized, and execution-oriented Chief of Staff to work directly with the CEO and leadership team.

This role sits at the center of strategy, finance, operations, and executive communications. The successful candidate will help drive key initiatives, improve organizational effectiveness, support board and executive reporting, and ensure the CEO and leadership team are operating with clarity and focus.

This is an ideal opportunity for someone with experience in strategic finance, business operations, corporate strategy, consulting, or a prior Chief of Staff role who wants broad exposure to company leadership and decision-making.

Role Overview

The Chief of Staff will serve as a strategic and operational partner to the CEO, helping translate priorities into action across the organization.

You will be responsible for preparing executive and board materials, supporting financial and operational planning, driving cross-functional initiatives, and helping leadership teams stay aligned on key business objectives.

The role requires strong analytical capabilities, excellent communication skills, sound business judgment, and a willingness to roll up your sleeves to get things done.

Key Responsibilities

Strategic & Executive Support

• Partner closely with the CEO on strategic initiatives and company priorities.
• Conduct business analysis and develop recommendations to support executive decision-making.
• Help identify and track key company objectives and strategic initiatives.
• Support leadership team planning and execution.

Board & Executive Communications

• Coordinate and prepare board presentations, executive updates, KPI reporting, and leadership meeting materials.
• Synthesize information from across the organization into concise, actionable insights.
• Ensure executive communications are accurate, professional, and delivered on time.
• Track action items and follow-up activities resulting from board and leadership meetings.

Financial & Business Performance Analysis

• Support budgeting, forecasting, and performance reporting processes.
• Develop and maintain dashboards and reporting packages for leadership review.
• Analyze company performance and identify trends, risks, and opportunities.
• Monitor key SaaS metrics including revenue growth, ARR, retention, customer acquisition, and operational performance.

Operational Excellence

• Drive execution of cross-functional initiatives and special projects.
• Establish processes and reporting structures that improve accountability and visibility.
• Coordinate activities across departments to ensure alignment and timely execution.
• Help remove organizational bottlenecks and improve operating effectiveness.

Qualifications

Required

• 5–10 years of experience in strategic finance, FP&A, business operations, corporate strategy, management consulting, investment banking, or Chief of Staff roles.
• Strong financial analysis and business modeling skills.
• Exceptional written and verbal communication skills.
• Advanced PowerPoint and presentation development capabilities.
• Ability to synthesize complex information into clear recommendations for executive audiences.
• Strong project management and organizational skills.
• Demonstrated ability to manage multiple priorities in a fast-paced environment.

Preferred

• Experience in SaaS, software, technology, or recurring-revenue business models.
• Experience preparing materials for executives, boards, investors, or senior leadership teams.
• Exposure to venture-backed, private equity-backed, or high-growth businesses.
• Experience working directly with C-level executives.

What Success Looks Like

Within your first year, you will:

• Become a trusted partner to the CEO and leadership team.
• Improve the quality and consistency of board and executive reporting.
• Increase visibility into company performance through stronger analytics and reporting.
• Successfully drive key cross-functional initiatives to completion.
• Help establish scalable processes that support continued company growth.

Desired Characteristics

• Entrepreneurial spirit
• Highly analytical and detail-oriented.
• Strong business and financial acumen.
• Excellent communicator and storyteller.
• Self-starter with a bias toward action.
• Comfortable working across functions and levels of the organization.
• Low ego, high accountability.
• Able to balance strategic thinking with hands-on execution.

Compensation

Competitive salary, annual performance bonus, and equity participation commensurate with experience.