Manager, Strategy and Transformation

Caseware combines over 35 years of industry expertise with AI-powered technology to transform how audit and accounting professionals work. Serving organizations across 130 countries, we bring intelligent automation directly into audit and financial reporting workflows—helping professionals reduce manual work, navigate complexity, and focus on informed decisions. Join our global team and help build technology that strengthens trust in financial information.

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

What's in it for you:

Shape what’s next with AI: Help transform audit and accounting through AI-powered technology. Explore new ways to bring AI into our own workflows, rethink how work gets done, and turn ideas into meaningful improvements for our teams and customers.

Make an impact that matters: Contribute to solutions that help professionals navigate complexity, make informed decisions, and strengthen trust in financial information around the world.

Bring your voice. Expand your perspective: Collaborate with a diverse global team where your ideas are valued, knowledge is shared, and different perspectives lead to better outcomes.

Build a career that grows with you: Develop your skills, take on new challenges, and explore career opportunities as our business and technology evolve.

Thrive at work and beyond: Enjoy competitive compensation, comprehensive benefits, recognition programs, and performance bonuses, alongside flexible work options, remote opportunities, and generous time off.

Many Voices, One Team:

We’re committed to building teams as diverse as our customers through equitable and inclusive hiring. We welcome candidates of all backgrounds. If you need accommodations or have questions at any stage of the application or interview process, contact our People Operations team at [email protected].

Background Check:

All successful candidates will undergo background screening, which may include identity verification, criminal record checks, and/or reference checks, as appropriate to the role and location and in accordance with applicable law.

Security and Fraud:

All employees are expected to apply security best practices and work within secure handling guidelines to perform assigned responsibilities when accessing data and business information.

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.