Entrepreneur in Residence – Technical Co-founder, CTO

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Take ownership of problem framing, architecture, system design, and product evaluation from the outset, converting vague product ideas into structured, contextual specifications that can be executed by both humans and AI systems.

• Leverage modern tools and cutting-edge models to operate swiftly without compromising on quality or maintainability, crafting agentic systems through first-principles reasoning, and discerning when orchestration provides significant leverage versus when simplicity is the optimal choice.

• Act as the primary technical representative during initial customer engagements, comprehending genuine workflows and shaping the appropriate product rather than merely rushing to deliver.

• Demonstrate the viability of a concept worth scaling before progressing to scalability, prioritizing traction before team expansion.

• Participate in fundraising activities, engaging in investor discussions and due diligence processes.

• Recruit and develop a technical team at the appropriate time, while also laying the cultural groundwork for the company.

⛳️ Requirements

• A proven history of delivering AI products to genuine users under real-world conditions — avoiding research, experiments, or prototypes.

• Extensive practical knowledge of frontier models, LLM-based systems, and agentic architectures, with a strong intuition for system design and a preference for simplicity and maintainability.

• Exceptional skills in translating complex product intentions into clear structures, constraints, and specifications that can be acted upon by both humans and AI systems.

• Customer-centric, comfortable in client discussions, and capable of allowing real workflows to inform your development process.

• Meticulous about verification — including feedback loops, evaluations, and establishing trustworthy systems.

• Prior experience as a technical co-founder or early engineering leader, with fundraising experience being a significant advantage.

• A true founder at heart — invigorated by uncertainty, capable of making significant progress independently, and ready to commit wholeheartedly.

🏝️ Benefits

• Opportunity to shape and influence cutting-edge AI products.

• Collaborative and innovative work environment.

• Competitive compensation and equity options.

• Flexibility in work arrangements to promote work-life balance.