Founding AI Engineer

Toronto Simple Ventures / Hybrid apply for this job About Simple Ventures We founded Simple Ventures (SV) with the mission of building great Canadian companies. Our thesis is simple: Canada is overlooked and under-appreciated. Most companies around the world ignore Canada because of perceived market size, regulation, language, and powerful oligopolies. As a result, Canadians miss out. But we know better. Canada is a top 10 global economy with many of the same consumer and business pain points as other markets. This creates an opportunity to bring the best product ideas to Canada - to see what’s working around the world and be first to execute for Canadians. We’re funded and supported by Canada’s top leaders including the founders and leaders of Wealthsimple, Shopify, Ada, MindBeacon, TD and many more. Our Approach We are experts in sourcing, vetting and launching new companies. Once we have conviction in a specific concept, we find the best fit CEO for the company and partner with them to accelerate and scale the venture. For CEOs, we significantly de-risk the prospect of starting a company. In particular, we help by: (a) validating the idea, (b) funding the concept, (c) unlocking a distribution advantage, and (d) bringing an extensive support network across product, engineering, marketing, and growth. For LPs, we seek to drive returns through disciplined validation and capital efficiency. Our approach is industry agnostic, with a focus on: (a) market validation, (b) speed to insight, (c) attractive unit economics, and (d) defensibility in the Canadian market. The Opportunity This is a founding technical role focused on embedding AI at the center of how new companies get built. You will act as the technical and AI backbone of the studio - building systems, tools, and products that dramatically increase the speed and quality of everything we do. Your work will directly increase the rate at which new companies are created. This is not a traditional CTO role. You are a builder first. You will be expected to move quickly, operate with high ownership, and push ideas from concept to working product in days, not weeks. You will work across the studio, portfolio companies, and new ventures - identifying opportunities for AI, building solutions, and creating leverage across a small team. This role is high ownership, high intensity, and fast-paced. You will be expected to operate with urgency, challenge how we work, and rebuild systems from first principles. There Are Three Main Aspects To The Role: Studio AI Infrastructure & Leverage Build AI-first systems, tools, and workflows that improve how the studio operates Identify bottlenecks across the team and eliminate them through automation or redesign Create leverage - your work should make the entire team faster and more effective Establish best practices and reusable infrastructure for how AI is applied across the studio Venture Building & Prototyping Rapidly prototype MVPs, features, and products for new venture concepts Turn ideas into functional products that can be tested with real users Use AI-native development workflows to compress build cycles from weeks into days Work closely with the venture team to validate ideas through real product and user interaction Portfolio Support & Applied AI Partner with CEOs and founders to identify high-leverage opportunities for AI Build or support the development of AI features, tools, and workflows within portfolio companies Distinguish signal from hype - focus on practical, high-impact applications of AI Help portfolio companies move faster by embedding AI into their core operations and products About You We’re looking for a high-agency technical builder with strong product instincts and a relentless drive to ship. You are AI-native, move quickly from idea to execution, and care deeply about building things that actually work and get used. You are motivated by speed, ownership, and creating leverage - not just writing code. You Should Have: Relevant Experience Experience building products, systems, or tools from scratch (startup, side project, or personal builds) Strong technical ability as an engineer, technical product builder, or exceptional generalist Experience working in fast-moving, early-stage environments (0→1 or 1→10) AI-Native Builder Actively use AI tools to build, prototype, and accelerate your work Experience with modern AI workflows (LLM APIs, agents, copilots, automation, etc.) Strong point of view on how AI changes how software and companies are built High-Velocity Execution Operates with urgency and intensity - you move quickly and don’t get stuck in analysis Bias for action - you ship fast and learn through real-world feedback Ability to run multiple workstreams in parallel without losing quality Product & Systems Thinking Strong product judgment - you know what is useful vs. noise Ability to move between problem framing and execution Thinks in systems - you look for ways to create leverage, not just complete tasks Ownership & Drive Relentless drive to build and win - you push until something works Extreme ownership - you take responsibility for outcomes, not tasks High standards - you care deeply about the quality and usefulness of what you build You are not a 9–5 operator - you are intrinsically motivated and think about problems beyond assigned work Communication & Collaboration Able to work closely with non-technical teammates and founders Clear communicator who can explain technical decisions and tradeoffs Comfortable challenging ideas and proposing better approaches This Role is Not for You If You prefer structured environments with clearly defined scope You need long planning cycles before building You are primarily focused on process over outcomes You are not deeply interested in AI or how it changes how software is built You optimize for stability or work-life balance over building Benefits & Perks Impact - Help build the next generation of Canadian companies Learning - Work closely with top founders and operators Ownership - Build across multiple ventures, not just one Benefits - Health & dental coverage Application Process As part of the process, you will be asked to build or prototype a small AI-driven product, workflow, or tool. This is the best way for us to understand how you think, build, and operate. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us. apply for this job Founding AI Engineer Toronto Simple Ventures / Hybrid apply for this job There Are Three Main Aspects To The Role: Studio AI Infrastructure & Leverage Build AI-first systems, tools, and workflows that improve how the studio operates Identify bottlenecks across the team and eliminate them through automation or redesign Create leverage - your work should make the entire team faster and more effective Establish best practices and reusable infrastructure for how AI is applied across the studio Venture Building & Prototyping Rapidly prototype MVPs, features, and products for new venture concepts Turn ideas into functional products that can be tested with real users Use AI-native development workflows to compress build cycles from weeks into days Work closely with the venture team to validate ideas through real product and user interaction Portfolio Support & Applied AI Partner with CEOs and founders to identify high-leverage opportunities for AI Build or support the development of AI features, tools, and workflows within portfolio companies Distinguish signal from hype - focus on practical, high-impact applications of AI Help portfolio companies move faster by embedding AI into their core operations and products You Should Have: Relevant Experience Experience building products, systems, or tools from scratch (startup, side project, or personal builds) Strong technical ability as an engineer, technical product builder, or exceptional generalist Experience working in fast-moving, early-stage environments (0→1 or 1→10) AI-Native Builder Actively use AI tools to build, prototype, and accelerate your work Experience with modern AI workflows (LLM APIs, agents, copilots, automation, etc.) Strong point of view on how AI changes how software and companies are built High-Velocity Execution Operates with urgency and intensity - you move quickly and don’t get stuck in analysis Bias for action - you ship fast and learn through real-world feedback Ability to run multiple workstreams in parallel without losing quality Product & Systems Thinking Strong product judgment - you know what is useful vs. noise Ability to move between problem framing and execution Thinks in systems - you look for ways to create leverage, not just complete tasks Ownership & Drive Relentless drive to build and win - you push until something works Extreme ownership - you take responsibility for outcomes, not tasks High standards - you care deeply about the quality and usefulness of what you build You are not a 9–5 operator - you are intrinsically motivated and think about problems beyond assigned work Communication & Collaboration Able to work closely with non-technical teammates and founders Clear communicator who can explain technical decisions and tradeoffs Comfortable challenging ideas and proposing better approaches This Role is Not for You If You prefer structured environments with clearly defined scope You need long planning cycles before building You are primarily focused on process over outcomes You are not deeply interested in AI or how it changes how software is built You optimize for stability or work-life balance over building Benefits & Perks Impact - Help build the next generation of Canadian companies Learning - Work closely with top founders and operators Ownership - Build across multiple ventures, not just one Benefits - Health & dental coverage Application Process As part of the process, you will be asked to build or prototype a small AI-driven product, workflow, or tool. This is the best way for us to understand how you think, build, and operate. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us. apply for this job

The role involves building AI-first infrastructure and tools to optimize studio operations and rapidly prototyping MVPs for new venture concepts. Additionally, the engineer will partner with portfolio CEOs to implement high-impact AI features and workflows within their companies.

Candidates must be high-agency technical builders with experience creating products from scratch in fast-paced, early-stage environments. Proficiency with modern AI workflows, LLM APIs, and a strong bias for high-velocity execution and ownership are essential.

• Health Coverage • Dental Coverage

• Product managementPreferred

Identified from the job description. Confirm important requirements above.

• AI Development
• Rapid Prototyping
• LLM APIs
• AI Agents
• System Architecture
• MVP Development
• Automation
• Product Management
• Software Engineering
• Technical Leadership
• AI Workflows
• Full-stack Development

• Software
• Technology
• Engineering
• Management & Leadership
• Data & Analytics

Minimum experience

5+ years

Apply by

Aug 19, 2026

Posting language

English

Working hours

40 hours per week

Seniority

Mid-Senior level