Project Manager – Enterprise Software Implementation

12–18 Month Contract | Remote-First | Greater Toronto Area

Contract Rate: $60–$80/hour CAD, based on experience and qualifications

Position Status: This posting is for an existing vacancy.

Location: Remote-first within the Greater Toronto Area, with occasional in-person meetings at TSG’s Thornhill office and client locations. Preference will be given to candidates located in the northern GTA who can readily attend in-person meetings when required.

Contract Term: Initial 12-month engagement with anticipated extension up to 18 months based on project requirements.

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About Us

The Siroky Group Inc. (TSG) is a Canadian software development and consulting company specializing in technology solutions for the Out-of-Home advertising industry.

TSG is seeking an experienced Project Manager to lead a significant, multi-phase enterprise software modernization initiative. The role will span project mobilization, discovery, design, development, incremental releases, UAT and implementation.

This is a hands-on delivery leadership role with direct interaction with senior TSG and client stakeholders. The successful candidate will have significant autonomy in establishing project governance, delivery practices, reporting and coordination across multiple concurrent workstreams.

Working closely with TSG’s executive, product, technical and development teams, the Project Manager will be responsible for translating an established Statement of Work and delivery roadmap into a structured, executable project plan.

The project will be delivered using an Agile approach within defined commercial, scope, timeline and milestone commitments. The successful candidate must therefore be comfortable balancing Agile delivery with the realities of a large enterprise implementation, including disciplined scope and change control.

• Establish and maintain the overall project plan, release schedule, milestones and dependencies.
• Translate contractual deliverables and timelines into manageable project workstreams, release plans and delivery activities.
• Coordinate activities across Business Analysis, UX/UI, architecture, development, QA, Dev Ops and client teams.
• Facilitate project kick-offs, planning sessions, status meetings, sprint/release planning and stakeholder reviews.
• Track project scope, schedule, budget, risks, issues, assumptions and dependencies.
• Maintain RAID logs and ensure risks and issues are actively managed and escalated when required.
• Work closely with Product Ownership and Business Analysis to ensure requirements and acceptance criteria remain aligned with contracted scope.
• Identify potential scope changes early, assess their impact and support the formal change-control process before additional work is undertaken.
• Coordinate client SME participation, decision-making, UAT, approvals and milestone acceptance.
• Monitor delivery against contractual milestones and support milestone acceptance and billing.
• Provide clear, concise project reporting to TSG leadership and client stakeholders.
• Coordinate third-party dependencies and integrations where required.
• Establish practical project governance that supports delivery without creating unnecessary administrative overhead.
• Support resource planning and identify capacity or scheduling risks before they impact delivery.
• Maintain clear project documentation, decisions, action items and accountability across workstreams.
• 7+ years of project management experience, preferably involving enterprise software development or implementation.
• Demonstrated experience managing complex, multi-stream software projects.
• Strong understanding of Agile software development and experience operating within fixed-price, fixed-scope or milestone-based commercial engagements.
• Experience working directly with enterprise clients and senior stakeholders.
• Strong understanding of the software development lifecycle, including requirements, UX, architecture, development, QA, UAT and production deployment.
• Experience managing integrations between multiple enterprise applications and third-party systems.
• Strong scope, risk, dependency and change-management skills.
• Ability to translate complex technical and business discussions into clear actions, decisions and project plans.
• Excellent written and verbal communication skills.
• Strong organizational skills with the ability to keep multiple workstreams moving simultaneously.
• Experience with Jira and modern project…