Director of Technology Project Management Office (PMO)

Medium; Toronto; On-site; CAD 110,000 - 145,000; Full time

Job summary

A leading SaaS organization in Toronto is seeking a highly motivated Director of Project Management Office to drive digital transformation and manage technology initiatives. This full-time, hybrid role involves aligning R&D projects with business strategy and ensuring compliance with IT policies. Required qualifications include 10+ years in IT project management and leadership experience. This role offers a competitive salary and benefits, along with a commitment to work-life balance and innovative culture.

Benefits

Flexible work options

Health insurance

Retirement plans

Performance bonuses

Career growth opportunities

Qualifications

• 10+ years in IT project management with 3-5 years in a leadership role.
• Experience managing large-scale technology portfolios.
• Ability to drive organizational change.

Responsibilities

• Align R&D and IT projects with business strategy.
• Oversee technology portfolio and project governance.
• Drive Agile transformation and ensure compliance.

Skills

IT project management

Leadership

Stakeholder management

Strategic thinking

Communication

Education

PMP or PgMP certification

Tools

Jira

Confluence

Job description

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 are seeking a highly motivated and detail-oriented Director of Project Management Office to join our R&D - Technology team at Caseware, a leading SaaS organization. As a Head of PMO, you will play a critical role in driving digital transformation, managing tech initiatives, and ensuring IT strategy execution.

❗This is a Full time 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 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 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, 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 [e-mail].

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.