Director of Technology Project Management Office (PMO)

Overview

Caseware is one of Canada's original Fintech companies, leading the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 languages. We are seeking a highly motivated and detail-oriented Director of Project Management Office to join our R&D - Technology team. As a Head of PMO, you will drive digital transformation, manage tech initiatives, and ensure IT strategy execution. This is a full-time hybrid role requiring the successful candidate to work 3 days a week in our Toronto office at 351 King Street East, Suite 1100, Toronto ON M5A 4T9. Contact: Taha Usmani – Senior Talent Acquisition Partner

What will you be doing

Align R&D and IT projects and programs with business strategy and digital goals. Partner with the CTO, engineering leaders, and business stakeholders. Drive Agile transformation and standardization, DevOps adoption, or hybrid delivery models.

Portfolio & Program Oversight

Oversee the technology portfolio including product, hosting/infrastructure, cybersecurity, and enterprise solutions delivery projects. Track progress, costs, benefits, and ROI of technology initiatives. Optimize resource allocation across programs. Partner with Product Operations Leader for end-to-end coordination of initiative delivery across R&D.

Governance & Compliance

Establish project governance frameworks tailored for tech (e.g., Agile, PMO, SAFe). Ensure compliance with IT policies, regulatory standards, and data governance.

Tooling & Reporting

Deploy and manage tools like Jira and Confluence. Create executive dashboards and real-time performance reports.

What you will bring

10+ years in IT project management with 3-5 years in a leadership role. Experience managing large-scale technology portfolios. PMP, PgMP certificate preferred. Leadership, communication, and stakeholder management skills. Strategic thinking and the ability to drive organizational change.

What's in it for you

▪️ Innovation is at our core.

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

— where your ideas are valued and knowledge sharing is encouraged within a supportive, inclusive team. ▪️ Work-life balance

— flexible work options, remote opportunities, and generous time-off policies to ensure a healthy balance. ▪️ Competitive compensation

— including salary and comprehensive benefits such as health insurance and retirement plans. ▪️ Impactful work

— your contributions affect how clients manage financial processes and drive success. ▪️ Recognition & rewards

— recognition programs, performance bonuses, and opportunities for career growth. ▪️ Global opportunities

— work on international projects with a diverse, global team.

About Caseware

Caseware's cutting-edge software products are designed for accounting firms, corporations, and governments. Our teams collaborate, innovate, and build on our suite of products with a customer-focused mindset to shape the future of audits, financial reporting, and data analytics. With a strategic investment from Hg Capital in 2020, Caseware is in a growth phase focused on people and products that drive success. We embrace Many Voices, One Team and are committed to diversity and inclusion. Candidates of all backgrounds are encouraged to apply. If accommodations or questions arise, please email Talent at Caseware.

Background Check

Successful candidates will complete a background check through Certn.co, typically including identity verification and criminal record check. Executives and Senior Managers may undergo a soft credit check. Candidates residing in the Netherlands or Germany are excluded from Certn.co background checks.

Security & Fraud

Caseware takes the security of candidates seriously. All legitimate communications will come from @caseware.com and positions are listed on reputable job boards and our website. We will never ask for payment or financial information. If you receive an unsolicited job offer, proceed with caution.

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