Technical Program Manager, AI Programs

We are seeking a Technical Program Manager (TPgM), AI Programs to drive the planning, coordination, and delivery of Caseware's AI roadmap across our Firm and Solution portfolios. This role sits at the center of our AI initiatives, turning a fragmented, hard-to-track view of AI work into a single trusted source of truth, and acting as the consistent unblocker that keeps AI programs moving from strategy through launch. 

You will partner across product, engineering, design, and go-to-market teams to manage AI launch programs end to end, surface and resolve dependencies before they become blockers, and give leadership clear, current visibility into where every AI initiative stands. If you are energized by bringing order to complex, cross-functional programs and by being the person who makes AI delivery predictable, this role is for you. 

This is an ideal opportunity for a program manager with strong technical fluency who wants to own high-visibility AI programs at scale and shape how a category leader builds and ships AI for assurance professionals. 

❗This is a New Role 

❗This is a full-time, permanent position. 

📍 Location: 

This position is available to all applicants eligible to work in Canada and residing in Toronto, Ontario. This is a hybrid role, working from office 3 days a week from our Downtown, Toronto office. 

• 3+ years in technical program management, product operations, or a related discipline in SaaS or platform environments, including cross-functional program delivery. 

• A track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality. 

• Strong technical fluency: able to engage credibly with engineering on AI/ML, APIs, data, and cloud architecture, and to translate between technical and business audiences. 

• Demonstrated ability to create clarity and a single source of truth in ambiguous, fast-moving environments. 

• Excellent stakeholder management, communication, and risk and dependency management skills. 

• Proven ability to drive outcomes across multiple teams without direct authority. 

Preferred Qualifications: 

• Experience managing AI/ML product or platform programs. 

• Familiarity with feature flagging, experimentation, or launch tooling (for example, LaunchDarkly). 

• Program management certification such as PMP, SAFe, or equivalent. 

• Degree in Computer Science, Engineering, or equivalent technical field. 

• Experience in fintech, audit, or regulated industries. 

The annual base salary for this position is between $110,000 and $130,00 CAD per year. 

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.