AI-Driven Strategy & Transformation Lead

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

Benefits offered by this job

Health insurance

Retirement plans

Flexible work options

Job summary

Caseware is seeking a Manager, Strategy and Transformation in Toronto to help guide strategic initiatives and monitor execution at the executive level. You will lead data-driven analyses and business cases, driving AI transformation across product, R&D, GTM, and corporate functions.

You will partner with Finance, Product, and other leaders to translate strategic direction into measurable execution, with hybrid work from the GTA and flexible arrangements for others.

Qualifications

• Experience in rigorous analytical environments such as management consulting or corporate strategy.
• Ability to drive cross-functional programs and influence senior stakeholders.
• Strong written and verbal communication with board-ready materials.

Responsibilities

• Advance Caseware’s highest-priority strategic initiatives across functions and regions.
• Lead data-driven analyses, business cases, and scenario modelling for priorities and investments.
• Drive AI transformation by coordinating initiatives across Product, R&D, GTM, and corporate functions.
• Apply AI-enabled tools to accelerate research, analysis, and program execution.
• Create executive-ready materials, narratives, updates, and KPI dashboards.
• Define outcomes, governance, milestones, metrics, and decision points for programs.
• Monitor progress and surface risks and interdependencies for executive review.
• Conduct targeted market, competitive, financial, and operational research.
• Partner with Finance, Product, R&D, Sales, Marketing, Revenue Ops, Customer Success, and People.

Skills

Analytical mindset

Executive communication

Strategy execution

Education

Bachelor’s degree in Business, Finance, Economics, or related field

Tools

Excel

PowerPoint

SQL

Tableau

Job description

Caseware is seeking a Manager, Strategy and Transformation in Toronto to help guide strategic initiatives and monitor execution at the executive level. You will lead data-driven analyses and business cases, driving AI transformation across product, R&D, GTM, and corporate functions.

You will partner with Finance, Product, and other leaders to translate strategic direction into measurable execution, with hybrid work from the GTA and flexible arrangements for others.