Remote Chief of Staff — AI & Operations Leader

Blue Orange Digital; New York (NY); Remote; USD 160,000 - 220,000; Full time

Benefits offered by this job

Health benefits

Equity or incentives

Remote-friendly work

Job summary

Blue Orange Digital is seeking an operator who thrives at the intersection of building intricate systems and managing end-to-end programs. You will report to the CEO with a dotted line to the CTO, coordinating between executive and engineering, product, and operations teams to align priorities.

In this role you will design and implement scalable AI workflows, de-risk leadership by removing single points of failure, and drive quarterly planning, OKRs, and cross-functional execution for ambitious

Qualifications

• 5+ years 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.

Responsibilities

• Build internal AI tools and automate internal processes.
• Transition AI workflows into company-wide programs with documentation and training.
• De-risk leadership by designing systems to offload single points of failure.
• Own the heartbeat of the company: OKRs, leadership cadence, and quarterly planning.
• Unblock cross-functional projects and drive initiatives to completion.
• Prepare strategic briefs and board materials; synthesize data into actionable narratives.

Skills

Program management

Systems thinking

AI/LLMs

Communication

Technical literacy

Tools

Python

SQL

APIs

Job description

Blue Orange Digital is seeking an operator who thrives at the intersection of building intricate systems and managing end-to-end programs. You will report to the CEO with a dotted line to the CTO, coordinating between executive and engineering, product, and operations teams to align priorities.

In this role you will design and implement scalable AI workflows, de-risk leadership by removing single points of failure, and drive quarterly planning, OKRs, and cross-functional execution for ambitious