Entrepreneur in Residence – Technical Co-founder (CTO)

FutureSight; Chicago (IL); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

Meaningful equity

Studio backing from day one

Own product and culture

Hands-on collaboration

Access to experienced founders

Continuous learning

Job summary

FutureSight is seeking an applied AI builder to co-found and lead the technical direction of a new B2B AI company from zero. You will frame problems, design systems, and build hands-on with frontier models to deliver practical, trusted solutions for customers.

You’ll engage early customers, shape product direction, and recruit when the time is right, contributing to fundraising and strategic decisions. This role is Chicago-based and highly entrepreneurial.

Qualifications

• You’ve shipped AI-enabled products that users actually adopt and trust.
• You bring strong technical and product taste, keeping systems simple and maintainable.
• You understand agentic architectures and know when orchestration adds value or noise.
• You can translate vague product intent into clear structure and specs for humans and AI.

Responsibilities

• Own the technical direction from day one: problem framing, architecture, design, and product judgement.
• Translate rough product intent into structure, context, and specs for humans and AI to execute.
• Build hands-on with modern tools and frontier models to move fast yet maintain quality.
• Be the primary technical voice in early customer conversations to shape the right product.
• Design and build agentic systems with first-principles thinking and appropriate simplicity.

Skills

Applied AI

Technical product sense

Agentic systems

LLMs / frontier models

System design

Customer empathy

Founder mindset

Shipping AI products

Fundraising

Job description

About FutureSight

FutureSight is a venture studio that co-creates and invests in B2B AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage by pairing hands‑on studio support with early‑stage capital — reducing risk and increasing the odds of success by 10x.

We’re a cross‑functional team of builders and investors. Our team includes Alan Smith (venture design), Prathna Ramesh (capital strategy), Dennis Ensing (operations and strategy), Krista LaRiviere (marketing and entrepreneurship, multi‑time exited founder), An Joshi (founder excellence), and John Carbrey, MD and Founder of FutureSight — a multi‑exit entrepreneur and experienced B2B SaaS operator who brings deep insight into what it takes to build and scale ventures from the ground up.

The Opportunity

We’re looking for an applied AI builder to co‑found and lead the technical direction of a new B2B AI company — from zero. Not someone who manages engineers from a distance or adds AI language to a traditional CTO resume. Someone who can take a vague problem, frame it clearly, design the right system, and turn it into something customers actually use and trust.

If you’ve gone from ambiguity to working product before — and you want to do it again with the backing of an experienced venture studio — read on.

What You’ll Do

• Own the technical direction from day one: problem framing, architecture, system design, and product judgement
• Translate rough product intent into structure, context, and specs that both humans and AI systems can execute against
• Build hands‑on — use modern tools and frontier models to move fast without sacrificing quality or maintainability
• Be the primary technical voice in early customer conversations: understand real workflows, shape the right product, not just ship quickly
• Design and build agentic systems with first‑principles thinking — knowing when orchestration adds genuine leverage and when simplicity is the better call
• Prove there is something worth scaling before thinking about scaling it — your first job is traction, not team‑building
• Recruit and grow a technical team when the time is right
• Contribute to fundraising — from investor conversations to due diligence

Requirements

• You’re an applied AI builder. You’ve taken AI capability and turned it into something users adopted, trusted, and got real value from — under real‑world constraints. Experiments and demos don’t count. Shipped products do
• You have strong technical and product taste. You keep systems simple, focused, and maintainable. You know when to move fast, when to slow down, and when to let the system run
• You understand agentic systems from first principles. You’re not impressed by orchestration complexity for its own sake. You know when it adds leverage and when it just adds noise — and you build accordingly
• You’re a strong translation layer. You can take messy product intent and turn it into clear structure, constraints, and specs that both humans and AI systems can act on. This comes from serious, hands‑on time with LLMs
• You’re close to the customer. You’re comfortable in customer conversations, understand real workflows, and let that shape what you build. You know that building the right thing is harder — and more valuable — than building fast
• You’re a founder at heart. Energized by ambiguity. Able to go far alone. Ready to commit fully
• Proven track record of shipping AI products to real users — not just research or prototypes
• Deep practical experience with frontier models, LLM‑based systems, and agentic architectures
• Strong system design instincts with a bias for simplicity and maintainability
• 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 is a strong plus

Benefits

• Meaningful equity — a true co‑founder stake with real upside as the company grows
• Studio backing from day one — early‑stage capital, operational support, and a team that’s done this before
• The chance to build something from scratch — own the product, the technical direction, and the culture of the company
• A partner, not just a platform — FutureSight is hands‑on. We build alongside you, not above you
• Access to an experienced network — tap into a team of multi‑exit founders, investors, and operators who are genuinely invested in your success
• Continuous learning and growth — tackle meaningful, high‑impact challenges at the frontier of what AI can do