Chief of Staff

Role Summary

The Chief of Staff – AI & Strategic Operations works closely with the Founder to turn company priorities, ideas, and challenges into clear plans and successful execution. This role requires someone who can take ownership of complex projects, research unfamiliar areas, evaluate solutions, and move initiatives forward with minimal direction.

Advanced AI proficiency is a core requirement for this position. The ideal candidate actively uses AI, automation, APIs, and technology in their everyday work to research, problem-solve, build workflows, improve processes, and execute more efficiently. This is not a coding role, but requires someone highly comfortable with technology and able to understand and coordinate technical projects.

Key Responsibilities

• Take ownership of strategic and operational projects from initial concept through implementation

• Turn broad objectives into clear project plans, timelines, requirements, and action items

• Use AI extensively for research, analysis, problem-solving, planning, documentation, and execution

• Build and utilize automations and AI-driven workflows to improve company operations

• Understand and work with APIs, integrations, webhooks, and connected systems

• Evaluate software, AI tools, vendors, consultants, and technology solutions

• Lead system and platform transitions by researching requirements, mapping processes, and coordinating implementation

• Identify opportunities to automate manual processes and improve operational efficiency

• Research unfamiliar topics quickly and determine the resources, expertise, and next steps required

• Coordinate developers, consultants, and technical specialists when specialized expertise is needed

• Identify project risks, dependencies, and potential problems before they impact execution

• Prepare research, recommendations, and options for Founder-level decisions

• Maintain ownership of active projects and ensure deadlines, deliverables, and follow-ups are completed

• Determine when projects can move forward independently and when Founder input or approval is required

Qualifications

• Advanced hands-on proficiency with AI tools and AI-driven workflows

• Demonstrated use of AI, automation, and technology as part of everyday professional work

• Strong working knowledge of automation tools, APIs, integrations, and modern software systems

• Experience building or managing automated workflows and technology-driven processes

• Strong project management and operational execution skills

• Proven ability to take an ambiguous objective and independently turn it into an actionable plan

• Ability to quickly research and understand unfamiliar systems, technologies, and business topics

• Technically proficient and comfortable working with developers and other technical specialists

• Strong analytical, problem-solving, and systems-thinking skills

• Comfortable working with spreadsheets, data, reporting, and business metrics

• Highly organized, dependable, and able to manage multiple projects simultaneously

• Strong judgment with the ability to verify AI-generated information and distinguish research from assumptions

• Excellent written and verbal communication skills

• Ability to work independently with minimal supervision and consistently follow projects through completion