Entrepreneur in Residence - Technical Co-founder (CTO)

FutureSight • Chicago, IL

1d • Remote

About The Position

FutureSight is seeking an applied AI builder to co-found and lead the technical direction of a new B2B AI venture from the ground up. This is a co-founder partnership with founder-level equity and founder-level authority, not a salaried executive role. The ideal candidate will be able to take a vague problem, frame it clearly, design the right system, and turn it into something customers actually use and trust. This is a full-time, exclusive commitment to building and owning a single B2B AI venture from the ground up. FutureSight is a leading venture studio that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. The studio team consists of experienced founders, operators, and designers with a track record of successfully bringing software to market at scale.

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.
• Fundraising experience a strong plus.
• Founder at heart — energized by ambiguity, able to go far alone, and ready to commit fully.

Responsibilities

• Set the technical direction of the venture and lead its execution.
• 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.

Benefits

• Founder-level equity with meaningful ownership from inception, aligned across funding rounds
• Founder-level authority, including co-decision rights on product, technology, hiring, fundraising, and strategy
• Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding
• A proven process and playbook for taking ventures from 0 to 1, informed by the studio team's prior experience and mistakes
• Studio resources, including embedded design, engineering, growth, and fundraising support from day one
• Investor and advisor network across B2B AI and early-stage capital markets

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed