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About the Role
Caseware is seeking a Technical Program Manager (TPgM), AI Programs to drive the planning, coordination, and delivery of Caseware's AI roadmap. This role will centralize AI initiatives, acting as a key unblocker to ensure AI programs progress from strategy to launch. You will partner with product, engineering, design, and go-to-market teams to manage AI launch programs, identify and resolve dependencies, and provide leadership with clear visibility into AI initiative status. This is an ideal opportunity for a program manager with strong technical fluency to own high-visibility AI programs and shape AI delivery for assurance professionals.
Responsibilities
- Own the AI Roadmap and its Single Source of Truth
- Maintain an authoritative, always-current view of the AI roadmap across Firms and Solution products, providing status, priorities, sequencing, and risk visibility.
- Establish and run the operating cadence (planning reviews, status reporting, roadmap updates) to keep stakeholders aligned.
- Translate AI strategy into sequenced programs with clear milestones, owners, dependencies, and success criteria.
- Drive AI Launch Programs
- Manage AI feature and capability launches end to end, coordinating product, engineering, design, marketing, enablement, and support.
- Build and maintain launch plans, readiness checklists, and go/no-go criteria, and track execution.
- Own cross-functional sequencing and dependency management to ensure timely and quality launches.
- Be the Consistent Unblocker
- Proactively identify dependencies, risks, and blockers across AI programs and drive them to resolution.
- Act as the point of connection between AI initiatives and dependent teams, escalating with clear context and options when decisions are needed.
- Reduce friction in decision-making by keeping trade-offs, owners, and open questions explicit and visible.
- Operational Excellence and Reporting
- Maintain program documentation, dashboards, and reporting for real-time visibility into AI roadmap health.
- Define and track program metrics such as delivery predictability, launch readiness, and adoption.
- Continuously 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.
- A track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality.
- Strong technical fluency: able to engage credibly with engineering on AI/ML, APIs, data, and cloud architecture, and to translate between technical and business audiences.
- Demonstrated ability to create clarity and a single source of truth in ambiguous, fast-moving environments.
- Excellent stakeholder management, communication, and risk and dependency management skills.
- Proven 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 (for example, 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.
- Successful completion of a background check.
Skills
- AI/ML
- APIs
- Cloud Architecture
- Stakeholder Management
- Communication
- Risk Management
- Dependency Management
- Feature Flagging
- Experimentation
- Launch Tooling
- PMP
- SAFe
Location
- Toronto, Ontario
- Downtown, Toronto office
Work Type
- Hybrid
- Full-time
- Permanent
Experience Level
- 3+ years
Education Level
- Degree in Computer Science, Engineering, or equivalent technical field.
Salary/Compensations
- $110,000 - $130,000 CAD per year
Benefits
- Discretionary bonus
- Commission
- Health insurance
- Retirement plans
- Flexible work options
- Remote opportunities
- Generous time-off policies
About the Company
- Caseware is a Canadian Fintech company with over 30 years of leadership in the global audit and accounting software industry, serving over 500,000 users in 130 countries.
- Caseware's cutting-edge software products are designed for accounting firms, corporations, and governments.
- The company is focused on innovation and collaboration, building technology that shapes the future of audits, financial reporting, and financial data analytics.
- With a strategic investment from Hg Capital in 2020, Caseware is in a major growth phase, doubling down on its people and products.
Equal Opportunity
- Caseware is dedicated to building teams as diverse as its customers in an equitable and inclusive way.
- The company welcomes and encourages candidates of all backgrounds to apply.
- The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.