Strategic Programs Lead, AI & Growth Initiatives

Caseware International; Toronto; Hybrid; CAD 125,000 - 145,000; Full time

Benefits offered by this job

Health insurance

Retirement plans

Flexible work options

Remote opportunities

Job summary

Caseware is seeking a Manager, Strategic Programs to join the Strategy team in Toronto. The role reports to the Chief of Staff and collaborates with the ELT to advance enterprise priorities through data-driven analyses and cross-functional execution.

You will help design, execute, and monitor AI-enabled strategic initiatives, develop board-ready materials, and drive governance across programs in a global fintech context.

Qualifications

• Bachelor’s degree in Business, Finance, Economics, or a related field.
• 3–6 years of experience in a rigorous analytical environment such as strategy or consulting.
• Strong analytical and financial acumen with data-driven decision experience.
• Proven ability to drive cross-functional programs and influence leaders.
• AI-forward approach with ability to validate outputs and improve processes.
• Proficiency with Excel and PowerPoint; familiarity with SQL/Tableau.

Responsibilities

• Support the Chief of Staff and ELT to advance high-priority strategic initiatives.
• Lead data-driven analyses, business cases, and scenario modelling.
• Contribute to AI transformation across Product, R&D, GTM, and corporate functions.
• Create executive- and board-ready materials and KPI dashboards.
• Define outcomes, governance, milestones, and decision points for programs.
• Monitor progress, surface risks, and coordinate executive attention.
• Conduct market, competitive, financial, and operational research.
• Partner with Finance, Product, R&D, Sales, Marketing, and People to translate strategy into execution.

Skills

Analytical thinking

Strategic thinking

Stakeholder management

Executive communication

AI literacy

Education

Bachelor's degree in Business, Finance, Economics, or a related field

Tools

Excel

PowerPoint

SQL

Tableau

Job description

Caseware is seeking a Manager, Strategic Programs to join the Strategy team in Toronto. The role reports to the Chief of Staff and collaborates with the ELT to advance enterprise priorities through data-driven analyses and cross-functional execution.

You will help design, execute, and monitor AI-enabled strategic initiatives, develop board-ready materials, and drive governance across programs in a global fintech context.