Position Overview

We are seeking an exceptional Chief of Staff to the CEO to serve as a strategic and operational force multiplier for a highly self-sufficient founder-CEO. This role is designed for a senior, experienced operator who can orchestrate strategy, drive execution, and enforce accountability across the leadership team.

This role exists to build and run the system around the CEO—ensuring priorities move from vision to execution, leaders stay aligned, and the company delivers against its goals as it scales.

This is a high-trust, high-impact role for someone who brings structure to speed, owns outcomes, and operates with confidence at the executive level.

Core Responsibilities

Strategic Orchestration & Execution

• Translate the CEO’s vision and company strategy into clear operating plans, goals, and milestones

• Drive company-wide planning processes (OKRs, quarterly planning, strategic reviews)

• Ensure enterprise initiatives progress on time, with clear ownership and measurable outcomes

• Identify execution gaps, risks, and bottlenecks early and drive resolution

Leadership Alignment & Accountability

• Keep the CEO and leadership team aligned, focused, and accountable to company goals

• Establish and run leadership operating rhythms (exec meetings, goal reviews, follow-ups)

• Ensure decisions made at the leadership level result in action and follow-through

• Act as a trusted, neutral enforcer of focus, priorities, and commitments

Ownership of Corporate Initiatives

• Independently own and execute cross-functional initiatives critical to company growth and scale

• Lead initiatives from concept through execution, coordinating across teams and stakeholders

• Track progress, surface insights, and report outcomes clearly to the CEO and leadership team

CEO Leverage (Not Support)

• Act as an extension of the CEO by managing information flow, context, and priorities

• Prepare the CEO with concise, high-signal briefs, insights, and recommendations

• Anticipate needs and proactively address issues before they escalate

• Step in as a proxy for the CEO when appropriate, reinforcing priorities and decisions

Operating System & Technology Enablement

• Build and refine lightweight systems that improve execution, visibility, and accountability

• Leverage technology, dashboards, and tools to scale how the company operates

• Drive adoption of processes and tools that increase clarity without adding bureaucracy

• Continuously improve operational effectiveness as the company grows

Ideal Candidate Profile

Experience & Background

• 8–12+ years of experience in Chief of Staff, strategy, operations, consulting, or equivalent roles

• Proven experience partnering closely with a founder or senior executive in a startup or high-growth environment

• Demonstrated ability to own complex, cross-functional initiatives end-to-end

• Experience operating in fast-paced, ambiguous, and resource-lean environments

Skills & Capabilities

• Strong strategic thinker with exceptional execution discipline

• Highly organized, decisive, and outcomes-oriented

• Confident communicator with the ability to influence senior leaders

• Highly tech-savvy; comfortable with modern productivity, project management, analytics, and AI tools

• Able to balance big-picture thinking with hands-on execution

Personal Attributes

• Proactive, anticipatory, and solutions-oriented

• Comfortable pushing leaders respectfully and holding the line on commitments

• High integrity, discretion, and sound judgment

• Low ego, high ownership, and bias toward action

• Calm and effective in ambiguity and change

What Success Looks Like

• Company priorities are clear, tracked, and consistently delivered

• Leadership meetings produce decisions and execution—not just discussion

• Strategic initiatives move faster and with greater predictability

• The CEO has leverage, clarity, and space to focus on the highest-impact work

Why This Role Matters

As the company scales, speed without structure becomes a bottleneck. This role ensures that focus, execution, and accountability scale with the business.

This is a foundational leadership role with significant visibility, trust, and long-term impact—not a support function.

Benefits

• 401k Matching

• Unlimited PTO

• Healthcare, Dental, Vision, and Life Insurance

• Paid parental/bereavement leave

• Home office stipend

Salary: $150,000 - $180,000

Background checks may be required for certain positions/projects.

Blue Orange Digital is an equal-opportunity employer.