Job Description

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're looking for a Technical Product Manager to own how Caseware builds, evaluates, and raises the quality of AI across the platform. You are the product owner of our core AI surfaces: the agents and agent builder practitioners use to do real work, the eval builder and eval roadmap that let us measure quality, and the agentic memory that lets the platform improve as it is used. You decide what we build, in what order, and whether it clears the bar before it reaches someone's audit file.

You are also the closest thing the product has to a practitioner in the room. Acting as an SME proxy, you carry the voice of the auditor into every decision: shadowing real workflows, validating outputs against what a qualified practitioner would actually sign off on, and turning "this doesn't feel right" into specific, actionable failure modes. You partner closely with applied scientists, engineering, domain experts, and external partner firms. You own the product outcome and the quality bar; the applied science team owns the science underneath it.

This role demands high agency. You'll operate with real autonomy, make decisions without waiting for permission, and own the outcome — success measured by results, not activity. You're intellectually curious, collaborate easily across teams, and take real pride in getting it right.

This work sits in the financial audit and assurance domain. Independent audit is one of the quiet foundations of the global economy — when investors, lenders, and regulators can trust that financial statements are accurate, capital flows and markets function. That trust rests entirely on the quality of the work, which is why the bar for AI here is so high. You don't need an accounting background to start, though one — or any real connection to the profession — adds high value. What you do need is genuine curiosity about the complexity of auditing and a deep appreciation for why quality is non-negotiable. You'll build that fluency on the job alongside experienced domain experts, and it will sharpen your judgment on what "good" really means.

❗This a full-time, permanent position

❗This a new vacancy

❗This role is hybrid. You will be required to work from our Toronto office 3-days a week, located at 351 King Street East, Toronto, ON

What you will be doing

• Own agents, the agent builder, the eval builder, and agentic memory as products: their roadmap, sequencing, and the business outcomes they drive, using results and practitioner feedback to shape what ships.
• Own the applied-science delivery roadmap and cross-team orchestration for the Caseware AI platform — sequence the evaluation, agentic-memory, and platform workstreams into a single plan, and keep delivery moving.
• Own the product acceptance bar for every AI feature — decide when an output is good enough to put in front of practitioners, and set the eval baseline so every agent and skill is measured against a stated bar.
• Embed with domain experts and partner accounting and audit firms to validate AI outputs against professional standards — not just user preferences, but what a qualified practitioner would actually sign off on.
• Be the voice of the practitioner as an SME proxy — shadow real audit workflows, test prototypes in context, and translate "this doesn't feel right" into specific, actionable failure modes the team can act on.
• Work daily with engineering to turn precise problem statements into well-scoped requirements, with acceptance criteria agreed before development begins.
• Stay ahead of the AI landscape — monitor model developments, new architectures, emerging agent patterns, and competitor moves, and bring a clear product point of view on what matters for Caseware.
• Define and own product health metrics for AI features: task completion, correction rates, override frequency, trust signals, and time-to-completion — and use them to drive product decisions.

What you will bring

• 6+ years of experience in technology-focused product management or product development, including 3–4 years working deeply with AI or machine learning–driven products. Software engineers transitioning into PM are welcome.
• Proven ability to drive delivery across multiple technical teams coordinating dependencies, shared interfaces, and timelines across applied-science, and platform-engineering pod.
• Direct experience building and running eval frameworks for production AI products: defining acceptance bars, running human-in-the-loop, practitioner validation, regression tracking across releases, and using results to decide what ships.
• Technical fluency in LLMs, RAG, prompt engineering, embeddings, and agentic patterns, enough to drive substantive conversations with engineers and know when a product problem is a model problem.
• High agency: you identify what needs to happen, move without waiting to be told, and take ownership of outcomes rather than just activities.
• Intellectual curiosity about AI — you follow model releases, read research, understand what frontier labs are shipping, and form your own views on what matters.
• Experience being the voice of the customer or practitioner: working with domain experts or subject matter specialists to define quality bars in high-stakes, regulated, or professional-grade contexts.
• Comfortable with ambiguity and energized by it. Many of the problems this role works on do not have clear playbooks, when there is no established benchmark for the work, you can go and find out how it should be measured.

Salary Range:

The annual base salary for this position is between $125,000 CAD and $135,000 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.