Project Manager, Professional Services

Project Manager

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

1. Lead end-to-end delivery of enterprise Caseware implementations, managing multiphase projects from kickoff through go-live and stabilization.
2. Establish and manage formal project governance, including steering committees, executive checkpoints, escalation paths, and decision-making frameworks.
3. Create and maintain project plans, managing scope, schedule, resourcing, dependencies, risks, and financials in alignment with Caseware Professional Services standards.
4. Act as the primary client-facing delivery lead, building trusted relationships with executive sponsors, finance leaders, IT teams, and audit stakeholders.
5. Coordinate cross-functional delivery teams, including Caseware consultants, product specialists, client resources, and third-party partners across multiple workstreams.
6. Proactively manage project risks, issues, and change requests, assessing impact and driving timely decisions to protect scope, schedule, and client outcomes.
7. Oversee enterprise data migration, integrations, and testing, ensuring data quality, security, and validation standards are met prior to go-live.
8. Provide clear executive-level reporting, communicating project status, risks, milestones, and financial performance to both client sponsors and internal leadership.
9. Drive client readiness and adoption, overseeing training coordination, change management activities, go-live planning, and transition to support and customer success teams.
10. 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.

Salary Range: The annual base salary for this position is between $106,000 CAD and $115,000 CAD per year. This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

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 talent@caseware.com.

AI Usage: The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.

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.