The Director of Strategic Programs will lead cross-functional initiatives to drive Caseware's enterprise transformation, focusing on strategic design and operational execution, while partnering with the executive team to enhance growth and performance.
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!
Caseware is seeking a 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.
This is not a purely advisory role. The mandate is intentionally split:
Phase 1: Strategic Design — Frame the problem, conduct rigorous analysis, and define the path forward
Phase 2: Operational Execution — Partner cross-functionally to implement initiatives and ensure measurable impact
You will operate as a senior individual contributor, with significant autonomy and executive exposure.
❗This is a New Role
❗This is a 12-month contract, full-time permanent position
📍 Location:
This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King St E, Toronto, ON.
What you will be doing:
- 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
What you will bring:
- 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
Why join the Office of CEO team:
- Executive Exposure: Partner closely with the CEO and Chief of Staff and gain insight into enterprise-level strategy and decision-making
- Strategic Ownership: Play a lead role in Caseware’s most mission-critical initiatives, from GTM acceleration to operational transformation
- Learning & Growth: Work alongside high-performing leaders from consulting, finance, and tech—sharpening your skills in strategy, operations, and execution
- Cross-Functional Impact: Operate at the intersection of Strategy, Finance, R&D, and GTM in a fast-paced, global SaaS environment
- Meaningful Mission: Help transform how auditors and financial professionals work—through modern, data-driven software that makes a difference
What's in it for you:
▪️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.
About Caseware:
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.
With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.
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. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at [email protected].
Background Check:
Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co
Security and Fraud:
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.
Caseware Toronto, Ontario, CAN Office
351 King St East, Suite 1100, Toronto, ON, Canada, M5V 1J6
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