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Technical Program Manager, AI Programs

CasewareToronto, ONProduct Ops & Release Management
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Salary
Not listed
Job type
Full Time - Permanent
Experience
Mid · 3+ yrs
Posted
2 Oct 2026
Status
Open · checked 7d ago

About this role

This Technical Program Management role suits a professional with a background in SaaS environments who wants to manage AI initiatives based in Toronto, ON. The position is ideal for someone skilled at driving complex cross-functional programs from strategy through launch.

Role Overview

Caseware seeks a Technical Program Management professional for its AI Programs team in Toronto, ON. The position focuses on overseeing the AI roadmap, coordinating cross-functional launches, and maintaining operational excellence across engineering, product, and business units.

Key Responsibilities

Maintain a single source of truth for the AI roadmap across Firms and Solution products, establishing planning reviews and status reporting.
Translate AI strategy into sequenced programs with defined milestones, owners, dependencies, and success metrics.
Manage end-to-end AI feature and capability launches by coordinating product, engineering, design, marketing, enablement, and support teams.
Identify and resolve dependencies, risks, and blockers across AI programs to prevent delivery delays.
Maintain program documentation, dashboards, and reporting to provide real-time visibility into roadmap health.

Requirements

Three or more years of experience in technical program management, product operations, or a related discipline within SaaS or platform environments.
Track record of orchestrating complex, cross-functional programs from strategy through launch on time and at quality.
Technical fluency to engage with engineering teams on AI/ML, APIs, data, and cloud architecture.
Ability to create clarity in ambiguous environments and drive outcomes across multiple teams without direct authority.

Nice to Have

Experience managing AI/ML product or platform programs.
Familiarity with feature flagging, experimentation, or launch tooling such as LaunchDarkly.
Program management certification like PMP or SAFe.
Degree in Computer Science, Engineering, or a related technical field.
Background in fintech, audit, or regulated industries.

Skills and Tools

AI/ML
APIs
Data architecture
Cloud architecture
LaunchDarkly

Salary and Benefits

Competitive salary and comprehensive benefits including health insurance and retirement plans.
Flexible work options, remote opportunities, and generous time-off policies.
Performance bonuses, recognition programs, and career growth opportunities.

About the Company

Caseware is a financial technology company that has served the global audit and accounting software industry for over 30 years. The company provides software products for accounting firms, corporations, and governments across 130 countries, supported by a strategic investment from Hg Capital received in 2020.

How to Apply

Candidates should apply on the official company careers page.

Skills and tech stack

AI/MLAPIsLaunchDarkly

Questions candidates ask

Where is this job located?

This position is located in Toronto, ON.

How many years of experience are required?

The role requires 3 or more years of experience in technical program management, product operations, or a related discipline in SaaS or platform environments.

What type of employment is this?

This is a full-time, permanent position.

Are background checks required for this role?

Yes, successful candidates must complete a background check through Certn.co, which includes identity verification and a criminal record check.

Ready to apply?

The application is on the official Caseware careers page.

Apply on company site