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 over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles Director, Strategic Programs (Contract) to join the Office of the CEO for a 12-18 month mandate. This is a senior, high-impact role designed for a strategy professional with 7-10 years of experience who is ready to operate inside the business and drive tangible enterprise value creation. You will work directly with the Chief of Staff and broader Executive Leadership Team (ELT) to design and execute critical elements of Caseware’s transformation agenda. This role sits at the center of enterprise-wide strategic priorities and will focus on identifying, shaping, and delivering initiatives that accelerate growth, improve revenue quality, and enhance operational performance. Strategic Design — Frame the problem, conduct rigorous analysis, and define the path forward You will operate as a senior individual contributor, with significant autonomy and executive exposure. This is a 12-month contract, 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 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 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 7+ years of experience in Management Consulting, Corporate Strategy, Private Equity portfolio operations, or a similar strategic or analytical role Why join the Office of CEO team: Strategic Ownership: Play a lead role in Caseware’s most mission‑critical initiatives, from GTM acceleration to operational transformation Help transform how auditors and financial professionals work—through modern, data‑driven software that makes a difference 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 growth opportunities. 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 are 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.

📌 Director, Strategic Programs (Toronto)
🏢 CaseWare
📍 Toronto