Director of AI Systems & Strategy

Role Summary

We are looking for an AI-native operator who will work directly with the founder to build the company's AI layer and transform ideas into scalable systems.

This is not a traditional CTO role. It is a unique hybrid of strategic thinking, technical execution, systems design, and AI innovation.

You will act as the founder's technical thought partner, helping design how AI, agents, knowledge systems, and automation become embedded across every layer of the company.

The ideal candidate naturally thinks through AI, agents, workflows, and systems. They rapidly prototype solutions, build internal tools, structure organizational knowledge, and continuously explore how emerging AI capabilities can improve decision-making, execution, and innovation.

What You'll Do

Build the Company's AI Layer

• Design and implement AI-native workflows across the organization.
• Build and deploy internal AI agents, copilots, and automation systems.
• Evaluate and integrate emerging AI tools, models, and platforms.
• Create systems that allow a small team to operate with outsized leverage.

Turn Ideas into Systems

• Work directly with the founder to convert concepts, opportunities, and strategic discussions into working prototypes and operational processes.
• Rapidly test, iterate, and deploy solutions.
• Act as a bridge between vision and execution.

Create Organizational Memory

• Design and maintain company knowledge infrastructure.
• Build centralized repositories for presentations, research, internal documents, and strategic
• assets.
• Develop AI-powered memory systems that preserve context and improve organizational learning.

Architect Data & Tooling

• Design the architecture connecting data, workflows, AI models, and internal tools.
• Ensure information is structured and accessible to both humans and AI systems.
• Create scalable foundations for future AI initiatives.

Bring AI into Strategic Decision-Making

• Ensure AI contributes to strategic discussions, planning sessions, and company-wide decision making.
• Develop systems that leverage LLMs not only for execution but also for idea generation, scenario analysis, and strategic thinking.
• Continuously experiment with new ways AI can augment leadership and innovation.

Ideal Background

You may come from various paths, including:

• AI Product Manager or Technical Product Manager
• Technical Founder or Startup Operator
• Applied AI Engineer
• AI Solutions Architect
• LLM Engineer or Agent Builder
• Technical Chief of Staff
• Automation Consultant
• Systems Designer
• Technical Program Manager with strong AI expertise

Most importantly, you have demonstrated ability to build useful systems, move quickly, and

leverage AI as a force multiplier.

What Success Looks Like

• AI becomes deeply embedded in company operations and decision-making.
• Organizational knowledge is structured, searchable, and continuously improving.
• Internal agents and tools save significant founder and team time.
• Strategic discussions are augmented by AI-generated insights and ideas.
• The company achieves leverage that would normally require a much larger team.

What This Role Is

• A founder's AI-native right hand.
• A builder of systems, agents, and organizational intelligence.
• A strategic thinker with hands-on execution skills.
• An operator focused on maximizing leverage through AI.

What This Role Is Not

• A traditional enterprise CTO.
• A people-management-heavy engineering leadership role.
• A purely operational project management position.
• A narrow automation specialist focused only on workflows.