Product Manager, AI Products at Caseware

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! 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. • 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. 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. • 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. 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 [Upgrade to PRO to see contact]. 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 [Upgrade to PRO to see link] We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.