Entrepreneur in Residence - Technical… at FutureSight · Toronto

The Opportunity

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.

We are not looking for someone who manages engineers from a distance or adds AI language to a traditional CTO resume. We are looking for 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 — this is the opportunity.

This is a full-time, exclusive commitment to building and owning a single B2B AI venture from the ground up.

About FutureSight

FutureSight is a leading venture studio that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

You'll co-create with a proven studio team, including:

• John Carbrey – 4x founder, bootstrapped to $100M ARR
• Joshua Auslander – Seasoned CFO and strategic advisor with $200M aggregate exits
• Alan Smith – Globally recognized early stage validation expert, 24 products launched, an exit, 5M+ books sold
• Prathna Ramesh – Early-stage investor and capital strategy advisor

The Partnership

• 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
• A true co-creation model in which you operate as CTO with the studio as your partner — building alongside you, not above you

Role & Responsibilities

As Co-Founder & CTO, you will set the technical direction of the venture and lead its execution. This is a co-founder role, not a CTO hire.

• Technical Direction — 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
• Build — 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
• Customer & Market — Be the primary technical voice in early customer conversations, understanding real workflows and shaping the right product rather than just shipping quickly
• Traction Before Scale — Prove there is something worth scaling before thinking about scaling it, focusing on traction first and team-building second
• Capital — Contribute to fundraising, from investor conversations to due diligence
• Team — Recruit and grow a technical team when the time is right, and establish the cultural foundation of the company

Co-Founder Profile

• 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

How to Apply

Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.