We are looking for a Product Manager to own the development of AI capabilities within the Caseware platform. You will work closely with engineering, domain experts, and external partner firms to define what we build, set a rigorous bar for quality, and ship AI that practitioners trust with real work.

This role requires high agency. You will operate with significant autonomy, drive decisions without waiting for permission, and take full ownership of outcomes. The right candidate is intellectually curious, stays genuinely close to developments in AI, and brings the judgment to know which new capabilities matter for our domain and which don't.

This is a full time position.

This is a New role.

Location:

This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, located at 351 King St E , Toronto, ON.

What you will be doing:

• Drive high-impact AI initiatives within the Caseware platform transformation - shape priorities and sequencing for your workstream, grounded in user research, domain expertise, and a clear view of technical feasibility.
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• Design and run rigorous eval frameworks: build golden datasets, define task taxonomies, write rubrics that score AI outputs the way a senior practitioner would, and run structured eval cycles before and after every major release.
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• Work daily with engineering to translate precise problem statements into well-scoped product requirements - including clear acceptance criteria and eval bars before development begins.
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• 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.
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• Drive continuous discovery with practitioners: shadow workflows, test prototypes in context, and turn 'this doesn't feel right' into specific, actionable failure modes.
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• Stay ahead of the AI landscape - monitor model developments, new architectures, emerging agent patterns, and competitor moves, and bring a clear point of view on what matters for Caseware.
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• 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.
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• Synthesize signals across engineering, partners, domain experts, customer success, and leadership into a coherent product direction - and communicate it with clarity at every level of the organization.
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What you will bring:

• 4+ years of experience in technology-focused product management or product development, including 1-2 years working deeply with AI or machine learning-driven products.
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• Direct experience building and running eval frameworks for AI products - golden datasets, rubrics, human-in-the-loop validation, and regression tracking across releases.
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• Technical fluency in LLMs, RAG, prompt engineering, embeddings, and agentic patterns - enough to have substantive conversations with engineers and know when a product problem is a model problem.
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• High agency: you identify what needs to happen, move without waiting to be told, and take ownership of outcomes rather than just activities.
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• Genuine curiosity about AI - you follow model releases, read research, understand what frontier labs are shipping, and form your own views on what matters.
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• Experience working with domain experts or subject matter specialists to define quality bars in high-stakes, regulated, or professional-grade contexts.
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• Comfortable with ambiguity. Many of the problems this role works on do not have clear playbooks - you are energized by that, not slowed down by it.
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Salary Range:

The annual base salary for this position is between $120,000 CAD and $130,000 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.