Caseware

Project Manager, Professional Services

Job Description

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. 
📍This is a hybrid role, requiring the successful candidate to work three days a week at our Toronto office  (351 King St E, 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 workstreams.
  • 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, workstreams, 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 a related field, or equivalent professional experience an asset.
  • Professional certifications such as PMP, PRINCE2, or equivalent; accounting or audit credentials (e.g., CPA, CA) are an asset.

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