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Manager, Strategy and Transformation

Caseware
Toronto, CAN
Full-time
Mid-Senior
Hybrid
CAD 125,000–145,000 per year
Discovered 3 days ago
Corporate strategyStrategic initiative managementData analysisBusiness cases and scenario modelingFinancial analysisAI tools

Full Job Posting

Role overview

Join Caseware's Strategy team, report to the Chief of Staff, and work closely with the Executive Leadership Team.

Advance strategic initiatives, lead data-driven analysis, and monitor execution against company goals.

This is a full-time, permanent vacancy.

What you'll do

  • Advance high-priority initiatives across functions, regions, and business units with the Chief of Staff and Executive Leadership Team.
  • Lead analysis, business cases, and scenario modeling to inform priorities, investment decisions, and resource allocation.
  • Coordinate measurable AI transformation initiatives across Product, R&D, go-to-market, and corporate functions.
  • Apply AI tools to research, analysis, synthesis, reporting, and program execution; identify broader operational improvements.
  • Prepare executive- and board-ready recommendations, performance narratives, initiative updates, and KPI dashboards.
  • Define program outcomes, governance, milestones, metrics, and decision points; monitor progress, risks, dependencies, and decisions requiring executive attention.
  • Conduct market, competitive, financial, and operational research.
  • Partner cross-functionally to turn strategic direction into measurable execution.

What you'll bring

  • Bachelor's degree in Business, Finance, Economics, or a related field.
  • 3–6 years of experience in management consulting, investment banking, corporate strategy, or a comparable analytical role.
  • Strong analytical and financial acumen; experience with complex datasets, models, research, and software metrics.
  • Ability to drive complex cross-functional programs and influence senior stakeholders without direct authority.
  • Clear communication and ability to translate complex issues into recommendations and actionable plans.
  • Experience using AI tools for research, analysis, synthesis, and content development; validate outputs with sound judgment.
  • Advanced Excel and PowerPoint proficiency; familiarity with SQL and Tableau is an asset.
  • Resourcefulness, organization, adaptability, professional maturity, and discretion.

Location and work arrangement

  • Greater Toronto Area candidates are preferred and work on a hybrid basis from the Toronto office.
  • Remote arrangements may be considered for candidates outside the Greater Toronto Area.

Compensation

  • Annual base salary is CAD 125,000–145,000 per year.
  • The role may also receive a discretionary bonus and/or commission, in addition to benefits.

About Caseware

Caseware develops accounting and financial reporting software for accounting firms, corporations, and governments, with products used globally.

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