Chief of Staff

Blue Orange Digital•New York, NY

12d•$150,000 - $180,000

About The Position

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.

Requirements

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
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
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

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