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Caseware

Technical Program Manager, AI Programs

Caseware

. Own and maintain the authoritative AI roadmap across Firms and Solution products .

Posted 10/5/2026full-timeToronto • CanadaMid-LevelSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in technical program management with a focus on AI/ML product and platform initiatives, ensuring successful cross-functional delivery and stakeholder engagement. Proficient in managing dependencies, risks, and metrics to drive program outcomes in fast-paced environments.

Highest-signal resume keywords
Technical Program ManagementAI/ML Product ManagementStakeholder ManagementProgram Management CertificationCross-Functional Program Delivery

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
AI/MLAPIsCloud ArchitectureProgram ManagementMetrics TrackingDependency ManagementRisk ManagementFeature FlaggingExperimentationLaunch Planning
Soft Skills
CommunicationStakeholder EngagementClarity CreationOutcome DrivingProblem Solving
Tools & Technologies
LaunchDarklyDashboardsRoadmap ToolsDocumentation Tools
Certifications & Qualifications
PMPSAFe
Industry Keywords
SaaSFintechAuditRegulated Industries

Tech Stack

Tools & technologies
CloudPMP

About the role

Key responsibilities & impact
  • 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

What you’ll need
  • 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

Benefits

Comp & perks
  • Flexible work options
  • Remote opportunities
  • Generous time-off policies
  • Competitive salary
  • Health insurance
  • Retirement plans
  • Recognition programs
  • Performance bonuses
  • Opportunities for career growth
  • International projects
  • Collaboration with a diverse, global team