Chief of Staff

Company Overview

Blue Orange Digital is a boutique data & AI consultancy that delivers enterprise‑grade results. We design and build modern data platforms, analytics, and ML/AI Agent solutions for mid‑market and enterprise clients across Private Equity, Financial Services, Healthcare, and Retail. Our teams work with technologies like Databricks, Snowflake, dbt, and the broader Microsoft ecosystem to turn messy, real‑world data into trustworthy, actionable insight.

We’re a builder‑led, client‑first culture that prizes ownership, clear communication, and shipping high‑impact work.

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.

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.

• Build internal AI, hands‑on. Get into the weeds of our internal AI tools. Prototype, test, and refine agentic workflows that automate our own internal processes, treating the company as the first customer of our technology.
• Turn AI work into a program. Transition experimental AI workflows into robust, company‑wide programs. Establish the documentation, training, and operational cadences required to make these systems reliable and scalable.
• Founder leverage and key‑person de‑risking. 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, dive in, identify the root cause, align 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.

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.

• Strategic Execution: running the weekly leadership sync, tracking OKRs, and clearing roadblocks for a stalled product launch.
• AI Implementation: prototyping a new LLM‑based workflow for customer support triage and designing the human‑in‑the‑loop review…