Product Manager, AI Products

Posted 2 weeks ago

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About the role

  • Product Manager for Caseware driving AI initiatives within the platform. Collaborating with engineering and domain experts to build trusted AI features for financial reporting.

Responsibilities

  • 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.
  • 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.
  • Work daily with engineering to translate precise problem statements into well-scoped product requirements — including clear acceptance criteria and eval bars before development begins.
  • 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.
  • Drive continuous discovery with practitioners: shadow workflows, test prototypes in context, and turn 'this doesn't feel right' into specific, actionable failure modes.
  • 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.
  • 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.
  • 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.

Requirements

  • 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.
  • Direct experience building and running eval frameworks for AI products — golden datasets, rubrics, human-in-the-loop validation, and regression tracking across releases.
  • 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.
  • High agency: you identify what needs to happen, move without waiting to be told, and take ownership of outcomes rather than just activities.
  • Genuine curiosity about AI — you follow model releases, read research, understand what frontier labs are shipping, and form your own views on what matters.
  • Experience working with domain experts or subject matter specialists to define quality bars in high-stakes, regulated, or professional-grade contexts.
  • 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.

Benefits

  • 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.

Job type

Full Time

Experience level

Mid levelSenior

Salary

Not specified

Degree requirement

Bachelor's Degree

Location requirements

HybridTorontoCanada

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