Technical Program Manager, AI Programs

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!

Own the AI Roadmap and its Single Source of Truth Maintain one authoritative, always-current view of the AI roadmap across Firms and Solution products, so leadership and teams know status, priorities, sequencing, and risk at any time without chasing updates. Establish and run the operating cadence (planning reviews, status reporting, roadmap updates) that keeps stakeholders aligned by default. Work with the team to translate AI strategy into sequenced programs with clear milestones, owners, dependencies, and measurable success criteria. Drive AI Launch Programs Manage AI feature and capability launches end to end, coordinating product, engineering, design, marketing, enablement, and support. Build and maintain launch plans, readiness checklists, and go/no-go criteria, and track execution against them. Own cross-functional sequencing and dependency management so launches ship on time and at quality. Be the Consistent Unblocker Proactively identify dependencies, risks, and blockers across AI programs and drive them to resolution before they slow delivery. Act as the point of connection between AI initiatives and the teams they depend on, escalating with clear context and options when decisions are needed. Reduce friction in decision-making by keeping trade-offs, owners, and open questions explicit and visible. Operational Excellence and Reporting Maintain program documentation, dashboards, and reporting that give real-time visibility into AI roadmap health. Define and track program metrics such as delivery predictability, launch readiness, and adoption. Continuously improve the AI program management operating model, templates, and tooling.

3+ years in technical program management, product operations, or a related discipline in SaaS or platform environments, including cross-functional program delivery. A track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality. Strong technical fluency: able to engage credibly with engineering on AI/ML, APIs, data, and cloud architecture, and to translate between technical and business audiences. Demonstrated ability to create clarity and a single source of truth in ambiguous, fast-moving environments. Excellent stakeholder management, communication, and risk and dependency management skills. Proven ability to drive outcomes across multiple teams without direct authority. Preferred Qualifications: Experience managing AI/ML product or platform programs. Familiarity with feature flagging, experimentation, or launch tooling (for example, LaunchDarkly). Program management certification such as PMP, SAFe, or equivalent. Degree in Computer Science, Engineering, or equivalent technical field. Experience in fintech, audit, or regulated industries.

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