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.

The Role

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.

Key Responsibilities

• 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, DevOps 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 collaboration/documentation tools.
• PMP, PMI-ACP, Scrum or similar certifications are considered an asset but are less important to us than demonstrated experience successfully delivering complex software projects.

What We’re Looking For

• 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 collaboration/documentation tools.
• PMP, PMI-ACP, Scrum or similar certifications are considered an asset but are less important to us than demonstrated experience successfully delivering complex software projects.

The Person We’re Looking For

You are organized without being bureaucratic.

You know when a meeting is necessary—and when a five-minute conversation will solve the problem.

You are comfortable challenging timelines, identifying risks and asking difficult questions when something does not look achievable.

You understand the commercial impact of scope decisions and can maintain a strong client relationship while ensuring that out-of-scope requests are identified and handled appropriately.

Most importantly, you understand that successful project management is not about maintaining a project plan. It is about creating clarity, keeping people aligned, identifying problems early and getting complex software successfully into the hands of users.

Contract Engagement

This engagement is intended for an individual contractor who will personally perform the role throughout the engagement. TSG is seeking a dedicated individual resource rather than an agency-based or rotating consulting model.

The engagement is expected to average up to 40 hours per week, based on project requirements.

If you are an experienced enterprise software Project Manager who enjoys bringing structure to complex initiatives while keeping delivery practical and moving forward, we would like to hear from you.

How to Apply:

Our online application will give you the option to apply to this role as a complete person – not just a resume. The application will assess your qualifications, personality traits and workplace preferences. It should take 10 to 15 minutes to complete. After submitting, you'll receive an email inviting you to log in and view your assessment results.

We will review applications submitted via the online application, with priority given to those who have completed the assessment. We will not consider or accept applications sent directly via email or standard post.

We thank everyone for their interest. We will only contact individuals selected for the next step in our hiring process.

Accessibility & Accommodations
TSG is committed to providing an accessible recruitment process. Accommodations are available upon request for applicants with disabilities throughout the recruitment and selection process. If you require an accommodation during this process press the help button and send us a note.