Description:
Caseware, a global leader in audit and accounting software with over 500,000 users in 130 countries, is seeking a highly motivated Director of Technology Project Management Office (PMO) to join their R&D Technology division. This hybrid role offers the opportunity to lead the execution of strategic IT and R&D initiatives that drive digital transformation, technological innovation, and portfolio governance across the enterprise.
The Director will play a central role in aligning IT projects with digital business goals, collaborating closely with the CTO, engineering leaders, and business stakeholders. The position also involves leading Agile transformation, DevOps standardization, and hybrid delivery models while overseeing enterprise-wide portfolios including product, infrastructure, cybersecurity, and enterprise solutions.
Key Responsibilities:
Align R&D and IT project portfolios with business strategy and digital transformation goals
Partner with engineering leaders and product operations teams for end-to-end delivery coordination
Oversee major tech project portfolios and track progress, ROI, costs, and resource allocation
Establish tech-specific governance models such as Agile, PMO, or SAFe
Ensure regulatory compliance and data governance adherence
Implement tools like Jira and Confluence for program management and executive reporting
Develop dashboards and real-time reports for leadership visibility
Required Qualifications:
10+ years of IT project management experience, with 3–5 years in leadership
Proven experience managing large-scale technology portfolios
PMP, PgMP certification (preferred)
Strong leadership, strategic thinking, and organizational change management skills
High-level communication and stakeholder management expertise
What Caseware Offers:
Exposure to cutting-edge SaaS innovation in audit and financial reporting
Collaborative, inclusive workplace with global team interactions
Flexible working options with work-life balance support
Competitive salary and comprehensive benefits (health insurance, retirement plans, bonuses)
Recognition programs and career advancement opportunities
International project opportunities
About Caseware:
Caseware has been an industry leader for over three decades, with significant growth and global expansion backed by a strategic investment from Hg Capital in 2020. The company emphasizes collaboration, innovation, and inclusion, building solutions for accounting firms, corporations, and governments worldwide. Diversity, equity, and accessibility are core to their hiring and working culture.
| Organization | Caseware |
| Industry | IT / Telecom / Software Jobs |
| Occupational Category | Director |
| Job Location | Toronto,Canada |
| Shift Type | Morning |
| Job Type | Full Time |
| Gender | No Preference |
| Career Level | Experienced Professional |
| Experience | 10 Years |
| Posted at | 2025-07-30 8:08 pm |
| Expires on | 2026-01-12 |