Program Manager, PMO (18-month contract)

Toronto, Canada /
Technology – Project Management Office /
Full Time - Permanent
/ Hybrid
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 International Inc. is seeking an experienced Program Manager to lead programs from conceptual design through implementation. You will be responsible for providing successful delivery and effective program/project management direction. The Program Manager will oversee program management, including oversight of the project delivery, managing the day-to-day activities of the PMO, manage both internal and external stakeholders, and collaborating with other departments. The Program Manager will leverage project management techniques to effectively manage complex projects with cross-functional teams on time and within budget.

The ideal candidate will have a deep understanding of project management methodologies and techniques, with a focus on Agile and Waterfall frameworks. They will have a strong track record of successfully managing complex software system implementation projects and possess excellent communication and stakeholder management skills. The Program Manager will be responsible for ensuring that  projects are delivered on time delivered on time, within budget, and to the satisfaction of all stakeholders. If you are a motivated and experienced Program Manager who is looking for an exciting challenge and growth opportunity, we encourage you to apply for this position.

In this role, you will be reporting to the Director of Strategic Programs. 

Chengeer Lee - Senior Talent Acquisition Partner

❗This is an IC (Individual Contributor) role 

❗This is a hybrid role: 3 days a week in the office are expected. Office location: 351 King Street East, Toronto, ON, M5C 2V6 

What you will be doing:

    • Leverage project management techniques to effectively manage complex projects with cross-functional teams on time and within budget
    • Ensure program budget is managed meticulously; create project burn reports, forecasting, variance analysis
    • Mitigate risk for programs by utilizing effective problem-solving techniques
    • Responsible for communication and status updates for programs
    • Devise and implement overall project strategy through various project phases
    • Implement strategies to ensure smooth transition/handover between project phases
    • Identifying opportunities for continuous improvement
    • Ensure appropriate reporting framework and metrics to monitor project performance against key KPIs (eg cost, timelines, quality etc)
    • Guide, implement and improve operational procedures and processes to optimize PMO
    • effectiveness
    • Responsible for translating organizational vision and goals to the PMO team. 
    • Monitor projects to ensure completion within a defined schedule, budget, and quality parameters
    • Interface with various functional groups, program/project teams and other stakeholders to effectively resolve issues and remove barriers to project success
    • Experienced in using both waterfall and agile frameworks of project management

What you will bring:

    • 5+ years of experience in program management
    • PMI and Agile familiarity required
    • Experience with post-merger integration/M&A processes and principles
    • Strong technical and organizational abilities
    • Strong leadership skills to align and motivate the team with diverse skills and points of view
    • Conflict resolution and advanced negotiations training a plus
    • Strong, direct and concise communications skills
    • Experience in managing multiple projects and/or programs simultaneously
    • Strong leadership skills with the ability to motivate and inspire cross-functional teams
    • Excellent communication and stakeholder management skills
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

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well.