Manager, Strategy and Transformation

We’re hiring a Manager, Strategy and Transformation to join our Strategy team, reporting directly to the Chief of Staff and working closely with the Executive Leadership Team (ELT).

This is a high-impact, high-visibility role at the centre of Caseware’s strategic evolution that will be involved in advancing key strategic initiatives, leading data-driven analyses, and monitoring execution against goals. You’ll combine strong business acumen, analytical horsepower, and structured problem-solving to help design, execute, and track the company’s most important cross-functional efforts.

This is a full-time, permanent position.

This is an existing vacancy.

Location:

Candidates based in the Greater Toronto Area (GTA) are preferred and will work on a hybrid basis from our Toronto office. Remote arrangements may be considered for candidates outside the GTA.

What you will be doing:

• Support the Chief of Staff and Executive Leadership Team 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 clear, 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.

What you will bring:

• Bachelor’s degree in Business, Finance, Economics, or a related field.
• 3-6 years of experience in a rigorous analytical environment, such as management consulting, investment banking, corporate strategy, or a comparable strategic role.
• Strong analytical and financial acumen, with experience using complex datasets, models, research, and software metrics to inform strategic and investment decisions.
• Demonstrated ability to drive complex, cross-functional programs and influence senior stakeholders without direct authority.
• Ability to navigate ambiguity, challenge conventional thinking, and translate complex issues into clear recommendations and actionable plans.
• Excellent written and verbal communication skills, including experience developing polished, executive- and board-ready materials.
• An AI-forward approach to work, with experience using AI tools to accelerate research, analysis, synthesis, and content development-while applying strong judgment to validate outputs and identify opportunities to improve how work gets done.
• Advanced proficiency in Excel and PowerPoint; familiarity with data and reporting tools such as SQL and Tableau is an asset.
• Highly resourceful, organized, and adaptable, with the professional maturity and discretion to manage multiple priorities and confidential matters in a fast-paced environment.

Why join the Office of CEO:

• Executive exposure: Support the CEO, Chief of Staff, and execution leadership team, gaining firsthand exposure to enterprise strategy and executive decision-making.
• Strategic ownership: Lead high-priority initiatives spanning AI transformation, go-to-market acceleration, strategic planning, and operational performance.
• AI-forward experience: Help shape how Caseware applies AI across its products and operations-and use emerging AI tools to rethink how strategic work, analysis, and execution get done.
• Cross-functional and global impact: Work at the intersection of Strategy, Finance, People Operations, R&D and GTM, collaborating with leaders and teams across Caseware’s global business.
• Accelerated learning and growth: Learn alongside experienced leaders from consulting, finance, and technology, while building skills in strategy, analytics, executive communication, and program leadership.

Salary Range

The annual base salary for this position is between $125,000 CAD and $145,000 CAD per year.

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically