Chief of Staff

Blue Orange Digital•New York, NY

15d•$160,000 - $220,000

About The Position

If you are fascinated by the cutting edge of agentic AI systems but fundamentally grounded in ruthless organization and driving cross-functional programs to the finish line, you are in the right place. We are a technical founding team, which means we all live in two worlds: building intricate systems and managing end-to-end programs. We are looking for an operator who thrives in that exact duality. You need to be detail-oriented and organized enough to jump into a dozen different functional areas on any given day, while remaining endlessly curious and excited to push the boundaries of what we can achieve with modern AI. At our core, we are systems thinkers. As we navigate this new frontier, we continuously return to first principles to ask a critical question: What is the AI's responsibility, and what is the human's? When you join us, you will be tackling multivariable complexity head-on. We will rely on your ability to break down our operations through systems design, helping us clearly define: The Guardrails: what processes require strict human monitoring, empathy, and intervention? The Leverage: what workflows can be tightened, fully automated, and confidently handed over to agentic AI? This role exists to act as the ultimate force multiplier for the founding team. As we scale our AI-driven systems, the complexity of our operations increases exponentially. We need a dedicated leader to bridge the gap between technical innovation (CTO) and strategic execution (CEO), ensuring that our internal AI capabilities are not just built, but effectively productized into operational programs that drive company-wide leverage and efficiency. You will report directly to the CEO, with a strong dotted line to the CTO. You will act as the primary liaison between the executive office and engineering, product, and operations teams, ensuring tight alignment across all business units.

Requirements

We are not looking for a traditional administrator. We are looking for an engineer of systems and processes. You should have a deep understanding of modern software development, API integrations, and LLM capabilities. While you may not write production code every day, you are highly technical and can hold your own in architecture discussions with the CTO.
5+ years of experience in high-growth tech, in roles such as Chief of Staff, Product Management, BizOps, or Engineering.
Proven track record of building and managing complex, cross-functional programs from 0 to 1.
Deep systems thinking capabilities; the ability to deconstruct a chaotic process and rebuild it into an optimized system.
Strong technical literacy, particularly regarding AI, LLMs, and agentic workflows.
Exceptional written and verbal communication skills, capable of distilling multivariable complexity into clear narratives.

Nice To Haves

Experience as a former founder or early-stage startup operator.
Hands-on experience scripting or building automations (Python, SQL, API integrations).

Responsibilities

Build internal AI, hands-on. Get into the weeds of our internal AI tools. You will prototype, test, and refine agentic workflows that automate our own internal processes, treating our company as the first customer of our technology.
Turn AI work into a program. Transition experimental AI workflows into robust, company-wide programs. You will establish the documentation, training, and operational cadences required to make these systems reliable and scalable.
Founder leverage and key-person de-risking. Systematically identify bottlenecks where the CEO or CTO are single points of failure. Design and implement systems, both human and AI-driven, to offload these responsibilities and de-risk the organization.
Operating cadence and company performance reviews. Own the heartbeat of the company. Manage OKRs, executive meetings, all-hands, and quarterly planning. Ensure everyone is aligned on the most critical priorities and tracking against our goals.
Cross-functional execution and unblocking. Serve as the ultimate unblocker. When cross-functional projects stall, you will dive in, identify the root cause, align the stakeholders, and drive the initiative to completion.
Strategic narrative and decision support. Prepare high-fidelity briefs, board materials, and strategic models. Synthesize complex multivariable data into clear, actionable narratives that enable fast, high-quality decision-making by the founders.
Responsible AI and operational guardrails. Define and enforce the boundary between human oversight and AI autonomy. Ensure all internal AI systems have appropriate monitoring, fail-safes, and ethical guardrails in place.
Exit readiness and operational maturity. Build the infrastructure, data rooms, and operational rigor required for future funding rounds, M&A, or an eventual exit, ensuring the company is always audit-ready.
Organizational health and talent. Monitor the pulse of the team. Partner with the founders on key leadership hires, resolve organizational friction, and cultivate a high-performance, systems-thinking culture.