Technical Program Manager owning Caseware's AI roadmap and cross-functional launches. Driving predictable delivery for Canada's audit and accounting software company.
Responsibilities
Own and maintain the authoritative AI roadmap across Firms and Solution products
Establish and run planning reviews, status reporting, and roadmap updates
Translate AI strategy into sequenced programs with milestones, owners, dependencies, and measurable success criteria
Manage AI feature and capability launches end to end across product, engineering, design, marketing, enablement, and support
Build and maintain launch plans, readiness checklists, and go/no-go criteria
Own cross-functional sequencing and dependency management
Identify dependencies, risks, and blockers and drive them to resolution
Connect AI initiatives with dependent teams and escalate decisions with clear context and options
Make trade-offs, owners, and open questions explicit and visible
Maintain program documentation, dashboards, and reporting
Define and track metrics including delivery predictability, launch readiness, and adoption
Improve the AI program management operating model, templates, and tooling
Requirements
3+ years in technical program management, product operations, or a related discipline in SaaS or platform environments, including cross-functional program delivery
Track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality
Strong technical fluency with AI/ML, APIs, data, and cloud architecture
Ability to translate between technical and business audiences
Ability to create clarity and a single source of truth in ambiguous, fast-moving environments
Stakeholder management, communication, risk and dependency management skills
Ability to drive outcomes across multiple teams without direct authority
Experience managing AI/ML product or platform programs
Familiarity with feature flagging, experimentation, or launch tooling such as 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
Eligible to work in Canada and residing in Toronto, Ontario
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