Technical Program Manager, AI Programs
Role Overview
Drive planning, coordination, and delivery of Caseware's AI roadmap across firm and solution portfolios.
Turn fragmented AI program information into a trusted source of truth and keep initiatives moving from strategy through launch.
Partner across product, engineering, design, and go-to-market teams to manage launches and provide leadership visibility.
Key Skills for This Role
Full Job Posting
Role overview
Drive planning, coordination, and delivery of Caseware's AI roadmap across firm and solution portfolios.
Turn fragmented AI program information into a trusted source of truth and keep initiatives moving from strategy through launch.
Partner across product, engineering, design, and go-to-market teams to manage launches and provide leadership visibility.
Key responsibilities
- Maintain an authoritative AI roadmap with status, priorities, sequencing, and risks; run planning reviews and reporting cadence.
- Translate AI strategy into programs with milestones, owners, dependencies, and measurable success criteria.
- Coordinate end-to-end AI feature and capability launches, including readiness plans, checklists, and go/no-go criteria.
- Identify and resolve blockers, manage dependencies, surface trade-offs, and escalate decisions with context and options.
- Maintain documentation, dashboards, and reporting; track delivery predictability, launch readiness, and adoption.
- Improve program operating models, templates, and tooling.
Required qualifications
- At least 3 years in technical program management, product operations, or a related SaaS or platform discipline, including cross-functional delivery.
- Track record delivering complex cross-functional programs from strategy through launch, on time and at quality.
- Technical fluency in AI/ML, APIs, data, and cloud architecture, with ability to translate between technical and business audiences.
- Ability to create clarity in ambiguous environments; strong stakeholder, communication, risk, and dependency management.
- 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 tools such as LaunchDarkly.
- PMP, SAFe, or equivalent program-management certification; a Computer Science, Engineering, or equivalent technical degree.
- Experience in fintech, audit, or regulated industries.
Location and work arrangement
- Applicants must be eligible to work in Canada and reside in Toronto, Ontario.
- Hybrid role working from the downtown Toronto office 3 days per week.
Compensation
- Annual base salary is CAD $110,000–$130,000 per year.
- Eligible for discretionary bonus and/or commission and other benefits; actual pay depends on relevant factors.
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