Top AI Jobs in Toronto

Leads strategy, governance, modernization, and operational excellence for enterprise platforms and workplace technology. Oversees Google Workspace, ServiceNow, ERP, web, desktop, workflow automation, and AI initiatives; integrates systems, reduces technical debt, establishes SLAs and analytics, manages vendors and budgets, partners with executives, and leads platform engineering and management teams.

Leads proactive and reactive technical delivery for enterprise customers using Power Platform, SharePoint, and Microsoft 365. Evaluates customer environments, identifies resiliency and security issues, provides modernization and AI transformation guidance, and delivers data-driven recommendations. Coordinates support, account, and engineering teams, contributes to incident resolution and on-call rotations, conducts assessments and workshops, and improves service delivery processes.

Join Welo Data’s Swahili contributor network for potential remote AI projects involving text, image, or audio annotation; search, advertising, or chatbot evaluation; prompt creation; and cultural and linguistic accuracy review. Applicants must be native or near-native Swahili speakers based in Kenya, Tanzania, or the Democratic Republic of Congo, with English proficiency, digital-tool comfort, and strong attention to detail. Projects vary in duration and compensation, with details provided before participation.

Own the strategy, roadmap, and delivery of digital customer support products, including chatbots, virtual assistants, self-service journeys, knowledge management, and AI capabilities. Improve customer outcomes, self-service adoption, and support efficiency through analytics and continuous optimization. Manage vendors, governance, compliance, and responsible AI standards while partnering cross-functionally with Operations, Technology, Customer Experience, Data, Product, Risk, and Compliance teams. Define success metrics and communicate product performance and outcomes to leadership.

Leads complex federal proposal and pursuit efforts, including RFP analysis, win strategy, capture planning, content development, compliance, scheduling, quality control, and interview preparation. Develops pursuit-specific marketing campaigns, presentations, qualification materials, and client positioning while coordinating cross-functional teams and leadership. Supports account management, public relations, thought leadership, opportunity tracking, and brand-building initiatives across multiple geographies.

Lead and develop a team of software, machine learning, and infrastructure engineers. Grow technical leaders, manage performance and hiring, remove systemic bottlenecks, clarify priorities, and own team outcomes. This player-coach role requires staying technically engaged, shaping engineering culture and processes, and helping the team use AI effectively in software development. Experience building AI in production and managing senior or staff-level engineers is required.

Lead execution on ambiguous, high-stakes technical problems across real-time AI workflows, reliability, AI infrastructure, healthcare integrations, and security. Make architectural decisions, de-risk strategic projects, drive initiatives to completion, establish engineering standards, apply product judgment, and improve team effectiveness through strong technical leadership and mentorship.

Own end-to-end strategy, roadmap, discovery, delivery, adoption, safety, and commercial readiness for AI-native cybersecurity products. Lead 0-to-1 launches with engineering, design, and go-to-market teams; establish experimentation, evaluation, and engagement programs; incorporate customer and partner feedback; manage AI quality and trust; and communicate product decisions and results to executives and field teams.

Develop AI-driven products through hands-on software development and product engineering. Build minimum viable products, solve problems creatively, and help shape future AI applications. The role is available remotely or in Boston and Chicago, with contract options ranging from two weeks to three months or full-time, plus potential revenue sharing.

Build and own production AI systems as the founding technical engineer within Jobber’s Office of the CEO. Architect systems end to end, including LLMs, retrieval, agents, integrations, permissions, security, reliability, and quality. Embed with teams to deliver AI into real workflows, evaluate build-versus-buy decisions, run rapid proofs of concept, and establish trustworthy AI standards. The role requires executive communication, pragmatic technology choices, and Staff-plus experience delivering systems used daily at scale.

Manage mid-market and enterprise customer accounts, leading onboarding, training, business reviews, engagement campaigns, renewals, and expansion coordination. Build stakeholder relationships, demonstrate product ROI, address objections, analyze usage data, deliver presentations and demonstrations, troubleshoot technical issues, and advocate for customer feedback internally. The role requires SaaS customer success or account management experience, strong communication and sales skills, and familiarity with HubSpot and Stripe.

Leads strategic customer engagements involving agentic AI, AI-powered applications, application architecture, modernization, and cloud-native development. Designs solutions through architecture sessions, demonstrations, prototypes, proofs of concept, and pilots. Coordinates Microsoft technical teams and partners, creates repeatable technical assets, influences technical sales opportunities, coaches peers, and supports production deployment outcomes.

Supervise and develop a B2B sales team supporting an AI advertising platform. Drive account expansion, customer satisfaction, portfolio performance, pipeline growth, and achievement of business targets. Coach Sales Executives, build agency relationships, manage complex sales cycles, analyze performance metrics, and present strategic reviews to client decision-makers. Collaborate with learning and development teams to support employee growth and execute long-term commercial strategies.

Lead the architecture and end-to-end delivery of enterprise IVR, routing, conversational AI, generative AI, and agentic virtual agent solutions. Responsibilities include developing bots, designing integrations, optimizing speech experiences, leading Agile delivery, establishing testing and deployment practices, advising customers, delivering training, and providing technical leadership. The role requires extensive experience with Dialogflow, Lex, enterprise APIs, architecture, software development, and customer-facing technical consulting.

Own the vision, roadmap, execution, and quality measurement for Clio’s AI Search platform. Lead engineering and ML teams developing hybrid lexical and semantic search across documents, emails, and records. Improve relevance through ranking, query understanding, embeddings, A/B testing, click-through analysis, and offline evaluations. Coordinate across Clio products while balancing relevance, latency, cost, permissions, and customer AI preferences. Translate customer search needs into measurable product improvements and guide both new product development and platform scaling.

Manage a portfolio of enterprise ecommerce customers, driving SaaS product adoption, AI and automation implementation, workflow optimization, account health, renewals, and expansion. Build stakeholder relationships, conduct check-ins and QBRs, identify churn risks, maintain customer data, and collaborate with Sales, Product, and Support teams to improve customer outcomes and internal playbooks.

Own a portfolio of approximately 40 enterprise customers, including complex named accounts. Build executive relationships, lead QBRs, drive AI and automation adoption, guide implementations, manage customer health and retention, identify expansion opportunities, and coordinate with Sales, Product, and Support to deliver measurable outcomes.

Lead media innovation and AI strategy for Mazda within the WPP Open ecosystem. Develop strategic narratives, high-level technology solution designs, and client value propositions. Serve as a trusted advisor on data, audience, media, and AI initiatives; coordinate cross-functional teams, identify and escalate issues, demonstrate ROI, and provide thought leadership on data-driven marketing and emerging AI solutions.

Lead strategic product and growth partnerships with Big Tech, legal technology firms, ISVs, and other technology partners. Build and prioritize a high-value deal pipeline, negotiate complex agreements, collaborate with Product, Engineering, GTM, Legal, and Compliance, and develop partnership monetization strategies. Mentor business development and partnership teams while driving measurable revenue, lead generation, product alignment, and long-term partner value.

Leads Agile delivery across multiple teams or complex value streams, facilitating Scrum ceremonies, coaching teams, resolving impediments, managing dependencies and risks, and aligning stakeholders. The role oversees backlog and sprint goals, delivery metrics, release and change management, governance, reporting, and continuous improvement. Experience with analytics programs, cloud platforms, and tools such as Azure DevOps, Jira, Confluence, and Miro is valuable.

Lead complex enterprise customer engagements involving secure, resilient, AI-enabled Azure solutions. Advise executives and technical leaders, improve solution health, performance, and availability, resolve critical incidents, and drive cloud adoption and business value. Deliver proactive assessments, workshops, guidance, and support while collaborating with account, engineering, and support teams. Influence product roadmaps, identify growth opportunities, mentor technical talent, lead projects, and contribute to customer success strategies and on-call support.

Lead the transformation of a profitable legal services company into an AI-native consumer law platform. Own the product and technology roadmap, build AI workflows across practice areas, improve the client portal, support law firm acquisitions, and hire and develop engineering, product, design, and data teams. The CTO will remain hands-on with coding while setting priorities and scaling the platform.

Develop customer-specific AI solutions for consequential business decisions. Investigate internal and public information, evaluate evidence, identify uncertainty, and design reliable AI workflows. Work directly with customers to understand needs, prototype solutions, test them with users, and improve their usefulness. Translate successful workflows into repeatable product capabilities while partnering with engineers on integrations and missing technical functionality.

Leads multiple software development teams building Redwood’s enterprise SaaS automation platform. Responsibilities include technical leadership, distributed-system architecture, engineering process improvement, Agile delivery, cloud-native development, CI/CD and observability, AI-assisted software development, hiring, mentoring, capacity planning, and engineering KPI reporting. The role partners with product, sales, customer success, and executive stakeholders to align engineering priorities and scale resilient, fault-tolerant Java-based services.

Build and ship LLM-powered and agentic features across a SaaS product, including conversational experiences, document understanding, maintenance guidance, and contractor matching. Integrate model APIs and agent frameworks using Python and TypeScript, own features from design through production monitoring, and establish testing and evaluation practices for LLM behavior. Collaborate with product and engineering teams to identify and deliver valuable intelligent capabilities.