Technical Program Manager, AI Programs

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

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

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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.

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

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

Drive AI Launch Programs

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

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

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

Be the Consistent Unblocker

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

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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.

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

Operational Excellence and Reporting

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

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

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

What you will bring:

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

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

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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.

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

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

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

Preferred Qualifications:

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Experience managing AI/ML product or platform programs.

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

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

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

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Experience in fintech, audit, or regulated industries.

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:▪️Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.

▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.

▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance.

▪️We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans.

▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success.

▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth.

▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team.

About Caseware:

Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.

With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.

One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com.

AI Usage:

The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.

Background Check:

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co

Security and Fraud:

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.