Project Manager, Professional Services

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 Linked In profiles!

The Project Manager within Caseware Professional Services leads complex, client-facing implementations of Caseware solutions for enterprise and large-market customers. You will be responsible for delivery excellence, stakeholder leadership, and governance across long-duration projects, partnering closely with clients and internal teams to ensure successful outcomes. You will lead a project team of Consultants, Technical Services, and Trainers to develop project plans that align with requirements.

You will also communicate effectively with clients and internal teams and facilitate the day-to-day operational aspects of the project, including scope, budget, and timeline. The role also partners cross-functionally with Sales, Product, Support, and Customer Success teams to deliver a successful project. The Project Manager will report to the Director of Professional Services.

❗This is a new role.

❗This is a full-time, permanent position.

Thisisahybridrole,requiringthesuccessfulcandidatetoworkthreedaysaweek at our Toronto office (351

KingStE,Toronto,ON).

What you will be doing:

Lead end-to-end delivery of enterprise Caseware implementations, managing multiphase projects from kickoff through go-live and stabilization.

Establish and manage formal project governance, including steering committees, executive checkpoints, escalation paths, and decision-making frameworks.

Create and maintain project plans, managing scope, schedule, resourcing, dependencies, risks, and financials in alignment with Caseware Professional Services standards.

Act as the primary client-facing delivery lead, building trusted relationships with executive sponsors, finance leaders, IT teams, and audit stakeholders.

Coordinate cross-functional delivery teams, including Caseware consultants, product specialists, client resources, and third-party partners across multiple work streams.

Proactively manage project risks, issues, and change requests, assessing impact and driving timely decisions to protect scope, schedule, and client outcomes.

Oversee enterprise data migration, integrations, and testing, ensuring data quality, security, and validation standards are met prior to go-live.

Provide clear executive-level reporting, communicating project status, risks, milestones, and financial performance to both client sponsors and internal leadership.

Drive client readiness and adoption, overseeing training coordination, change management activities, go-live planning, and transition to support and customer success teams.

Manage project financial performance, including budget tracking, forecasting, billing milestones, scope control, and change orders, ensuring projects are delivered in line with contractual commitments and margin targets.

What you will bring:

5+ years of experience managing client-facing software implementation projects, ideally within professional services, SaaS, or enterprise technology environments.

Demonstrated experience leading long-duration, complex projects (9–12 months) with multiple stakeholders, work streams, and dependencies.

Strong understanding of project management methodologies and ability to apply structured delivery frameworks in regulated environments.

Proven ability to engage and communicate effectively with senior client stakeholders, including executives, finance leaders, and IT management.

Experience managing project financials, including scope control, change management, forecasting, and margin awareness.

Excellent written and verbal communication skills, with the ability to deliver executive-level status reporting and facilitate governance meetings.

Strong organizational, risk management, and problem-solving skills, with a track record of driving projects to successful outcomes.

Bachelor’s degree in Business, Accounting, Finance, Information Systems, or related…