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.

What you will be doing:

Own the AI Roadmap and its Single Source of Truth

• Maintain one authoritative, always-current view of the AI roadmap across Firms and Solution products, so leadership and teams know status, priorities, sequencing, and risk at any time without chasing updates.

• Establish and run the operating cadence (planning reviews, status reporting, roadmap updates) that keeps stakeholders aligned by default.

• Work with the team to translate AI strategy into sequenced programs with clear milestones, owners, dependencies, and measurable success criteria.

Drive AI Launch Programs

• Manage AI feature and capability launches end to end, coordinating product, engineering, design, marketing, enablement, and support.

• Build and maintain launch plans, readiness checklists, and go/no-go criteria, and track execution against them.

• Own cross-functional sequencing and dependency management so launches ship on time and at quality.

Be the Consistent Unblocker

• Proactively identify dependencies, risks, and blockers across AI programs and drive them to resolution before they slow delivery.

• Act as the point of connection between AI initiatives and the teams they depend on, escalating with clear context and options when decisions are needed.

• Reduce friction in decision-making by keeping trade-offs, owners, and open questions explicit and visible.

Operational Excellence and Reporting

• Maintain program documentation, dashboards, and reporting that give real-time visibility into AI roadmap health.

• Define and track program metrics such as delivery predictability, launch readiness, and adoption.

• Continuously improve the AI program management operating model, templates, and tooling.

What you will bring:

• 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.