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.

About the Role

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.

Reporting and Relationships

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.

Responsibilities

• 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.

What We’re Looking For

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.

A Week in the Life

• 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 process.
• Founder Support: drafting a board deck on our AI leverage metrics and ghostwriting an internal memo from the CEO on system guardrails.

Qualifications

Required

• 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.

Preferred

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

Compensation and Benefits

• Base Salary: $160,000 to $220,000, adjusted based on experience and geography.
• Equity / Incentive: 0.5% to 1.0%, commensurate with impact and seniority.
• Benefits: comprehensive health, dental, vision, and wellness stipends.

What Success Looks Like

In your first 90 days, you will have successfully mapped our core operational bottlenecks, taken over the weekly leadership operating cadence, and deployed at least one internal AI workflow that tangibly saves the founding team time.

Long‑term success means you have built a scalable, AI‑leveraged operational machine where the founders are fully de‑risked from day‑to‑day firefighting, allowing the company to move faster and smarter than our competition.

Location: Remote - United States

Background checks may be required for certain positions/projects.

Blue Orange Digital is an equal‑opportunity employer.