Entrepreneur in Residence – Technical Co-founder, CTO

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🔥 0 minutes ago

🌽 Illinois – Remote

🌽 Illinois – Remote

⏰ Full Time

🟡 Mid-level

🟠 Senior

👨‍💼 Chief Technology Officer (CTO)

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FutureSight

WebsiteLinkedInAll Job Openings

11 - 50 employees

🤖 Artificial Intelligence

🤝 B2B

Venture Capital • Artificial Intelligence • B2B

FutureSight is a venture studio that co-founds and funds B2B AI ventures, building scalable world-class businesses with values-driven leaders. Based in Toronto, New York, and San Francisco, FutureSight collaborates with entrepreneurs by providing a supportive community of experienced product leaders, business designers, engineers, marketers, and growth hackers. This 'Dream Team' aids in refining ideas from inception to scale, developing co-founders into transformational leaders. FutureSight focuses on various sectors, including health tech, education tech, and fintech, offering a rigorous process for validating ideas and investing in great talent and concepts.

📋 Description

• Own problem framing, architecture, system design, and product judgment from day one, translating rough product intent into structure, context, and specs that both humans and AI systems can execute against • Use modern tools and frontier models to move fast without sacrificing quality or maintainability, designing agentic systems with first-principles thinking and knowing when orchestration adds genuine leverage versus when simplicity is the better call • Be the primary technical voice in early customer conversations, understanding real workflows and shaping the right product rather than just shipping quickly • Prove there is something worth scaling before thinking about scaling it, focusing on traction first and team-building second • Contribute to fundraising, from investor conversations to due diligence • Recruit and grow a technical team when the time is right, and establish the cultural foundation of the company

🎯 Requirements

• Proven track record of shipping AI products to real users under real-world constraints — not research, experiments, or prototypes • Deep practical experience with frontier models, LLM-based systems, and agentic architectures, with strong system design instincts and a bias for simplicity and maintainability • Strong translation layer skills — able to turn messy product intent into clear structure, constraints, and specs that both humans and AI systems can act on • Close to the customer, comfortable in customer conversations, and able to let real workflows shape what you build • Rigorous about verification — feedback loops, evaluation, and systems that can be trusted • Prior experience as a technical co-founder or early engineering leader, with fundraising experience a strong plus • Founder at heart — energized by ambiguity, able to go far alone, and ready to commit fully