Caseware

Director, Strategic Programs – Contract

Caseware

contract

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

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Job Level

Lead

About the role

  • Lead high-priority, cross-functional initiatives tied to Caseware’s enterprise transformation agenda
  • Execute and support strategic initiatives under the direction of the Chief of Staff, including analysis, synthesis, and preparation of materials for ELT
  • Drive structured, hypothesis-led problem solving across growth, efficiency, and operating model evolution
  • Build robust business cases and financial models to inform executive trade-offs and investment decisions in alignment with defined operational processes
  • Develop executive- and board-ready materials that clearly articulate strategy, risks, trade-offs, and expected impact
  • Stand up and manage PMO discipline across select enterprise programs, bringing rigor, transparency, and accountability
  • Track progress against defined KPIs, identify risks and interdependencies, and drive resolution with initiative owners
  • Partner across Finance, R&D, Sales, Marketing, RevOps, Customer Success, and People to ensure alignment and execution pace

Requirements

  • 7+ years of experience in Management Consulting, Corporate Strategy, Private Equity portfolio operations, or a similar strategic or analytical role
  • Strong critical thinking and problem-solving skills, with a strategic mindset and ability to challenge the status quo
  • Demonstrated ability to move from strategic design to hands-on, cross-functional execution
  • Highly resourceful, adaptable, and capable of navigating ambiguity
  • Excellent written and verbal communication skills, with the ability to distill complex issues into clear messages
  • Ability to produce polished executive-ready deliverables
  • High degree of discretion, professionalism, and ownership
Benefits
  • Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.
  • We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.
  • Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance.
  • We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans.
  • We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success.
  • Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth.
  • We embrace global opportunities. Work on international projects and collaborate with a diverse, global team.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
financial modelingbusiness case developmentKPI trackingproblem solvingstrategic analysisexecutive communicationcross-functional executionPMO managementoperational processesrisk identification
Soft Skills
critical thinkingstrategic mindsetadaptabilityresourcefulnesscommunicationprofessionalismownershipambiguity navigationcollaborationexecutive presence