Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles! We’re hiring a Manager, Strategic Programs 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 a hybrid role, requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King Street East, Toronto, Ontario. 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.

Monitor progress against company priorities, proactively surfacing risks, interdependencies,



and decisions requiring executive attention. Partner with leaders across Finance, Product, R&D;, Sales, Marketing, Revenue Operations, Customer Success, and People to translate strategic direction into measurable execution. Bachelor’s degree in Business, Finance, Economics, or a related field. ~3–6 years of experience in a rigorous analytical setting, 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. ~ 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 Lead high-priority initiatives spanning AI transformation, go-to-market acceleration, strategic planning, and operational performance. 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. Learn alongside experienced leaders from consulting, finance, and technology, while building skills in strategy, analytics, executive communication, and program leadership.

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. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.

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. Your contributions directly affect how our clients manage financial processes and drive their success. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth.

Work on international projects and collaborate with a diverse, global team. Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products.

With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like. One of Caseware's core values is Many Voices, One Team and with that in mind, we’re dedicated to building teams as diverse as our customers in an equitable and inclusive way. co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well.

Security and Fraud com and our open positions are always listed on reputable job boards and on our website We will NEVER ask for payment or financial information from you.

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