headstart jobs in Toronto

42 headstart job listings in Canada. Find daily updated positions from leading job boards.


  • Toronto, ON, Canada Urban Ridge Supplies Full-time €367,000 - €389,000 Contract

    Become an Applied AI Engineer at Headstart, where you can work remotely while driving innovative AI solutions. Engage in complex technical challenges, leading projects from ideation to deployment. In this impactful role, you will lead multifaceted engagements, bringing together diverse technical stacks and influencing strategic client decisions. You will...


  • Toronto, ON, Toronto Census Division, ON; Ontario, Canada Urban Ridge Supplies Full-time

    Become an Applied AI Engineer at Headstart, where you can work remotely while driving innovative AI solutions. Engage in complex technical challenges, leading projects from ideation to deployment. In this impactful role, you will lead multifaceted engagements, bringing together diverse technical stacks and influencing strategic client decisions. You will...


  • Toronto, ON, Toronto Census Division, ON; Ontario, Canada Headstart AI Full-time

    Headstart AI is seeking a Senior Engineering Manager to lead engineers, shape architecture, and drive staffing across client engagements in the US and Canada. You'll start on a client engagement to learn the work, then build and lead a team as we grow. You’ll own recruiting, staffing, and partnerships with product and client stakeholders, guiding...


  • Toronto, ON, Canada Urban Ridge Supplies Full-time €191,000 - €318,000 Contract

    About The Company Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR) shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply. We've built our own...


  • Toronto, ON, Canada Headstart AI Full-time

    Headstart AI is seeking a Senior Engineering Manager to lead engineers, shape architecture, and drive staffing across client engagements in the US and Canada. You'll start on a client engagement to learn the work, then build and lead a team as we grow. You’ll own recruiting, staffing, and partnerships with product and client stakeholders, guiding technical...


  • Toronto, ON, Canada Urban Ridge Supplies Full-time €191,000 - €318,000 Contract

    Headstart seeks an experienced engineer to own client engagements end-to-end, from discovery to production of AI systems across multiple domains. You will translate enterprise problems into concrete technical scopes and ship reliable AI solutions, contributing to platform patterns and infrastructure. Expect collaboration across teams, code reviews, and a...


  • Toronto, ON, Canada Urban Ridge Supplies Full-time €367,000 - €389,000 Contract

    About The Company Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply. We are building our...


  • Toronto, ON, Toronto Census Division, ON; Ontario, Canada Urban Ridge Supplies Full-time

    Headstart seeks an experienced engineer to own client engagements end-to-end, from discovery to production of AI systems across multiple domains. You will translate enterprise problems into concrete technical scopes and ship reliable AI solutions, contributing to platform patterns and infrastructure. Expect collaboration across teams, code reviews, and a...


  • Toronto, ON, Toronto Census Division, ON; Ontario, Canada Urban Ridge Supplies Full-time €225,000 Temporary

    About The Company Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR) shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply. We've built our own...


  • Toronto, ON, Toronto Census Division, ON; Ontario, Canada Headstart AI Full-time €300,000 Temporary

    About The Company Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform...


  • Toronto, Ontario, Canada Headstart AI Full-time

    About The CompanyHeadstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to...