Product Manager, AI Products

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. 

• 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.