Technical Program Manager, AI Programs

Caseware combines over 35 years of industry expertise with AI-powered technology to transform how audit and accounting professionals work. Serving organizations across 130 countries, we bring intelligent automation directly into audit and financial reporting workflows—helping professionals reduce manual work, navigate complexity, and focus on informed decisions. Join our global team and help build technology that strengthens trust in financial information.

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: 

What you will bring:

Salary Range: 

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. 

What's in it for you:

• Shape what’s next with AI: Help transform audit and accounting through AI-powered technology. Explore new ways to bring AI into our own workflows, rethink how work gets done, and turn ideas into meaningful improvements for our teams and customers. 

• Make an impact that matters: Contribute to solutions that help professionals navigate complexity, make informed decisions, and strengthen trust in financial information around the world. 

• Bring your voice. Expand your perspective: Collaborate with a diverse global team where your ideas are valued, knowledge is shared, and different perspectives lead to better outcomes. 

• Build a career that grows with you: Develop your skills, take on new challenges, and explore career opportunities as our business and technology evolve. 

• Thrive at work and beyond: Enjoy competitive compensation, comprehensive benefits, recognition programs, and performance bonuses, alongside flexible work options, remote opportunities, and generous time off. 

Many Voices, One Team:

We’re committed to building teams as diverse as our customers through equitable and inclusive hiring. We welcome candidates of all backgrounds. If you need accommodations or have questions at any stage of the application or interview process, contact our People Operations team at [email protected].

Background Check:

All successful candidates will undergo background screening, which may include identity verification, criminal record checks, and/or reference checks, as appropriate to the role and location and in accordance with applicable law.

Security and Fraud:

All employees are expected to apply security best practices and work within secure handling guidelines to perform assigned responsibilities when accessing data and business information. 

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.