Job title: Technical Program Manager - AI Enablement

If you can hold your own in an Azure architecture discussion and still run a clean sprint review the same afternoon, you're exactly who we're looking for.

We're currently hiring for a contract opportunity with a respected organization in the Information Technology sector. You'll own end-to-end delivery across Azure and on-premises environments, leading Agile teams and working with engineering, product, business, finance, risk, and compliance stakeholders in a regulated financial environment. What matters most is a strong technical background in Azure combined with 7+ years of hands-on Agile project management experience. If you're also curious about using AI tools to cut manual work in reporting, documentation, and risk tracking, that's a real bonus. This is a hybrid role based in Toronto: candidates from anywhere in Canada are welcome to apply, as long as they can work onsite in Toronto. The contract runs until December 2027, with steady Monday-to-Friday hours, and independent contractors are welcome. If you're a technical PM who loves bringing order to complex delivery, we'd love to hear from you.

TalentWorld is recruiting a Technical Program Manager - AI Enablement in Toronto, Ontario for one of our partners.

Why Work with TalentWorld

TalentWorld understands time is crucial for you; therefore, we offer a contract running until December 2027, with a straight Monday-to-Friday schedule between 8:00 AM and 5:00 PM, so you can keep a consistent routine.
Independent contractors are welcome to apply.
Hybrid work arrangement in Toronto, balancing time onsite with working from home. Candidates from anywhere in Canada are welcome but must be able to work onsite.
An enticing hourly wage range of $65/HR - $75/HR, with flexibility for candidates with a strong technical background




Accurate and always on-time weekly payday
We advocate for our workers, ensuring that every environment is safe
We understand that life happens, just connect with us as soon as something comes up.

Technical Program Manager - AI Enablement Responsibilities

Own end-to-end program management for Azure and on-premises environments, from intake and planning through delivery and closure
Apply Scrum, Kanban, and SAFe across multiple teams, facilitating cross-team ceremonies and coaching teams on Agile and DevOps principles (CI/CD, flow metrics, WIP management)
Identify and implement AI-enabled tools and workflows, such as automated status reporting, AI-assisted risk and dependency identification, meeting synthesis, and documentation generation
Maintain roadmaps, RAID logs, dashboards, and executive reporting, with an eye toward automation and self-service
Align priorities with engineering, product, business, and finance stakeholders, and manage escalations while balancing technical, business, and regulatory requirements

Technical Program Manager - AI Enablement Qualifications

Must have:

Strong technical background in Azure, with comfort discussing infrastructure, migrations, platform services, and operations with engineering teams
7+ years of experience as an Agile Project or Program Manager, applying Scrum, Kanban, or SAFe to plan and deliver work across technical teams
Able to work onsite in Toronto, Ontario as required

Nice to have:





Experience with on-premises infrastructure, and with Jira and Confluence for program tracking and documentation
Practical experience using AI tools (generative AI assistants, GitHub Copilot, Windsurf, Visual Studio Code) to improve reporting, documentation, or workflow automation
Experience in financial services, banking, or another highly regulated industry
PgMP, SAFe Agilist, ACSM, KMP, or an equivalent certification
Cloud governance, cost optimization, or FinOps experience

Even if you don't think you check all the boxes, let's talk. If you bring robust Azure expertise and Agile project management experience, we want to hear from you. We know that your resume doesn't tell the whole story.

Tools and Methods

Methods: Scrum, Kanban, SAFe, CI/CD, flow metrics, WIP management
Planning and documentation: Jira, Confluence, roadmaps, RAID logs, dashboards
Platforms: Azure and on-premises infrastructure
AI tools: Generative AI assistants, GitHub Copilot, Windsurf, Visual Studio Code

Employment Details

Schedule: Monday to Friday, between 8:00 AM and 5:00 PM
The location: Toronto, Ontario (hybrid); candidates from anywhere in Canada are welcome but must be able to work onsite
Other: Contract until December 2027; independent contractors welcome

Interested in Technical Program Manager - AI Enablement role in Toronto, Ontario?
Apply now!

We are currently hiring for this role for one of our client organizations.

TalentWorld is a Canadian leader in staffing, offering diverse opportunities for professional growth, flexible schedules, and career advancement. Embracing diversity, all are welcome to apply.

Please note that AI tools may be used to support the screening, assessment, or selection of applicants for this position.

#TWPRA

📌 Technical Program Manager - AI Enablement (Toronto)
🏢 TalentWorld
📍 Toronto