Technical Program Manager owning Caseware's AI roadmap and cross - functional launches. Driving predictable delivery for Canada's audit and accounting software company.
About the role
- Technical Program Manager orchestrating complex initiatives across products and platforms at PointClickCare. Ensuring clarity, alignment, and flow to deliver customer and business impact.
Responsibilities
- Enable product outcomes: Partner with Product and Engineering Leads to translate strategy and OKRs into coordinated execution plans, ensuring teams stay focused on delivering measurable customer and business value.
- Orchestrate multi-team initiatives: Lead cross-team efforts spanning product, infrastructure, and platform capabilities - ensuring alignment, dependency visibility, and sustainable flow.
- Drive clarity and flow: Remove ambiguity by connecting business intent to execution signals. Use delivery and outcome metrics to inform, not control, decision-making.
- Harness AI for insight: Use AI-driven analytics to surface risks, detect bottlenecks, and generate proactive recommendations that improve velocity and predictability.
- Champion empowered delivery: Coach teams on healthy operating rhythms and data-driven practices that balance autonomy with alignment.
- Bridge strategy to execution: Facilitate alignment between senior product, design, and engineering leaders - making trade-offs visible, decisions explicit, and accountability shared.
- Shape systems and culture: Contribute to how PointClickCare executes at scale, evolving shared tools, processes, and frameworks that amplify impact across the portfolio.
- AI fluency and curiosity: Understanding of applied AI concepts, comfort using AI tools to support analysis, documentation, and decision-making, and awareness of responsible and ethical AI practices in engineering environments.
- Travel to company Onsite -25% for eligibility
Requirements
- Bachelor’s degree in computer science, Engineering, or related field, or equivalent practical experience.
- 5+ years of experience leading complex software programs in TPM/EPM or similar roles.
- 3+ years driving multi-team initiatives across product and platform or infrastructure.
- Experience translating strategy and OKRs into execution plans, managing dependencies, risks, and delivery health signals.
- Proficient with program execution and delivery tooling (Jira, Confluence, Aha! or equivalents) for planning, dependency management, status reporting, and stakeholder visibility.
- Technical fluency in modern software systems (APIs, architectures, integration patterns) and ability to engage in technical design conversations.
- Experience using metrics to improve predictability, flow, and outcomes; comfort using AI tools to support analysis and decision-making.
Benefits
- Benefits starting from Day 1
- Retirement Plan Matching (RRSP & 401K)
- Flexible Paid Time Off
- Lifestyle/Wellness Spending Account
- Parental & Caregiver Leaves
- Fertility & Adoption Support
- Continuous Development Support Program
- Employee Assistance Program
- Learning Programs & Resources
- Employee Recognition … and more!
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