Entrepreneur in Residence - Technical Co-founder (CTO)

FutureSight • Toronto, ON

13h • 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. The partnership offers founder-level equity, meaningful ownership, and founder-level authority, including co-decision rights on product, technology, hiring, fundraising, and strategy. Pre-seed capital is 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, will be provided. Studio resources, including embedded design, engineering, growth, and fundraising support, will be available from day one, along with an investor and advisor network across B2B AI and early-stage capital markets. This is a true co-creation model where the co-founder operates as CTO with the studio as a partner.

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.
• Founder at heart — energized by ambiguity, able to go far alone, and ready to commit fully.

Nice To Haves

• Fundraising experience a strong plus.

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.
• Focus on traction first and team-building second, proving there is something worth scaling before thinking about scaling it.
• 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