Top AI & Machine Learning Jobs in Toronto, ON

Reposted YesterdaySaved
Remote or Hybrid
Toronto, ON, CAN
Expert/Leader
Expert/Leader
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex technical initiatives across teams, establish reliable and secure AI evaluation practices, make build-versus-buy decisions, and partner with Sales, Product, Data, and Engineering leaders. Mentor engineers, guide design and implementation, and use data and feedback to improve system adoption and business impact.
Top Skills: Ai AgentsCustomer Relationship Management (Crm) SystemsGoLarge Language Models (Llms)Retrieval SystemsTool CallingWorkflow Orchestration
Reposted YesterdaySaved
Remote or Hybrid
CA
Expert/Leader
Expert/Leader
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
Own the architecture and technical strategy for Square’s go-to-market systems. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations while establishing AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering leaders to translate business needs into scalable solutions, make build-versus-buy decisions, mentor engineers, and improve business impact through data and user feedback.
Top Skills: Ai AgentsCrm PlatformsGoLarge Language Models (Llms)RetrievalTool CallingWorkflow Orchestration
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