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Technical Program Manager, AI Programs

CaseWare International
Toronto, CAN
Full-time
Hybrid
$110,000–$130,000 per year
Discovered 2 weeks ago
Technical program managementAI/MLSaaS and platform environmentsCross-functional program deliveryAPIsData

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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