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Job Title


Entrepreneur in Residence - Technical Co-founder (CTO)


Company : FutureSight https://static.whatjobs.com/static/ajC


Location : Toronto, Ontario


Created : 2026-05-07


Job Type : Full Time


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 handson studio support with earlystage capital, reducing risk and increasing the odds of success by 10x. We're a crossfunctional team of builders and investors: Alan Smith (venture design), Prathna Ramesh (capital strategy), Dennis Ensing (operations and strategy), Krista LaRiviere (marketing and entrepreneurship, multitime exited founder), An Joshi (founder excellence), and John Carbrey, MD and Founder of FutureSight a multiexit 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 cofound and lead the technical direction of a new B2B AI company from the ground up. Youll create solutions rather than simply managing engineers or adding AI language to a traditional CTO resume. We value a candidate who can take a vague problem, frame it clearly, design the right system, and turn it into something customers actually use and trust. If youve 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 Youll Do Own the technical direction from day one: problem framing, architecture, system design, and product judgment Translate rough product intent into structure, context, and specs that both humans and AI systems can execute against Build handson 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 firstprinciples 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 teambuilding Recruit and grow a technical team when the right time comes Contribute to fundraising from investor conversations to due diligence Requirements Youre an applied AI builder. Youve taken AI capability and turned it into something users adopted, trusted, and got real value from under realworld constraints. Experiments and demos dont count; shipped products do. You have strong technical and product taste. You keep systems simple, focused, and maintainable, knowing when to move fast, when to slow down, and when to let the system run. You understand agentic systems from first principles. Youre not impressed by orchestration complexity for its own sake; you build accordingly. Youre 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, handson time with LLMs. Youre close to the customer. Youre 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. Youre 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, LLMbased 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 cofounder or early engineering leader. Fundraising experience is a strong plus. Benefits Meaningful equity a true cofounder stake with real upside as the company grows. Studio backing from day one earlystage capital, operational support, and a team thats 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 handson. We build alongside you, not above you. Access to an experienced network tap into a team of multiexit founders, investors, and operators who are genuinely invested in your success. Continuous learning and growth tackle meaningful, highimpact challenges at the frontier of what AI can do. #J-18808-Ljbffr