Strategy & Transformation Manager, AI-Driven Growth

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

Benefits offered by this job

Health insurance

Retirement plans

Flexible work options

Job summary

Caseware, a leading fintech company, is seeking a Manager, Strategy and Transformation to join the Strategy team. You will report to the Chief of Staff and work with the ELT to推进 key strategic initiatives, analytics and AI-driven transformation across Product, R&D, GTM, and corporate functions.

The role is full-time and hybrid with GTA preference. You will develop board-ready materials and KPI dashboards while ensuring governance, milestones, and risks are managed effectively in a fast-paced,

Qualifications

• Bachelor's degree in Business, Finance, Economics, or related field.
• 3–6 years of experience in rigorous analytical environment.
• Strong analytical and financial acumen with experience using complex datasets and metrics.
• Proven ability to drive cross-functional programs and influence senior stakeholders.
• Ability to navigate ambiguity and translate complex issues into clear recommendations.
• Excellent written and verbal communication, including executive-ready materials.
• AI-forward approach with experience using AI tools to accelerate research and analysis.
• Advanced proficiency in Excel and PowerPoint; familiarity with SQL/Tableau is a plus.

Responsibilities

• Support the Chief of Staff and ELT to advance Caseware’s highest-priority strategic initiatives across functions, regions, and business units.
• Lead data-driven analyses, business cases, and scenario modelling to inform strategic priorities, investment decisions, and resource allocation.
• Help drive Caseware’s AI transformation by translating enterprise priorities into coordinated, measurable initiatives across Product, R&D, GTM, and corporate functions.
• Apply AI-enabled tools and ways of working to accelerate research, analysis, synthesis, reporting, and program execution—while identifying opportunities to improve how the broader organization operates.
• Develop executive- and board-ready materials, including strategic recommendations, performance narratives, initiative updates, and KPI dashboards.
• Establish structure and accountability across complex, cross‑functional programs by defining outcomes, governance, milestones, metrics, and decision points.
• Monitor progress against company priorities, proactively surfacing risks, interdependencies, and decisions requiring executive attention.
• Conduct targeted market, competitive, financial, and operational research to support executive decision‑making.
• Partner with leaders across Finance, Product, R&D, Sales, Marketing, Revenue Operations, Customer Success, and People to translate strategic direction into measurable execution.

Skills

Analytical thinking

Financial acumen

Cross-functional leadership

Ambiguity navigation

Executive communication

AI-driven approach

Multitasking

Education

Bachelor’s degree in Business/Finance/Economics

Tools

Excel

PowerPoint

SQL

Tableau

Job description

Caseware, a leading fintech company, is seeking a Manager, Strategy and Transformation to join the Strategy team. You will report to the Chief of Staff and work with the ELT to推进 key strategic initiatives, analytics and AI-driven transformation across Product, R&D, GTM, and corporate functions.

The role is full-time and hybrid with GTA preference. You will develop board-ready materials and KPI dashboards while ensuring governance, milestones, and risks are managed effectively in a fast-paced,