About Us Datasite is the essential infrastructure for M&A.; Also comprising Grata, Blueflame AI, and Sherpany, we help dealbreakers find opportunities, manage transactions, and make key decisions.

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Job Description The Senior Manager of Strategic Project Management leads Datasite's highest-priority cross-functional initiatives from definition through delivery, including go-to-market readiness, acquisition integration, and business systems implementations. This leader brings structure, speed, and accountability to complex, ambiguous work, and uses AI-enabled tools and practices to plan, execute, and communicate more effectively. They partner with executives and functional leaders to turn strategy into measurable outcomes.

Duties And Responsibilities Program and Project Leadership

Own end-to-end delivery of multiple concurrent strategic initiatives, from business case and scoping through planning, execution, launch, and post-implementation review.

Lead go-to-market readiness efforts, such as new product and offering launches, pricing and packaging changes, and market expansion, coordinating Product, Sales, Marketing, Customer Success, Finance, Legal, and Operations.

Lead acquisition integration programs, including Day 1 readiness, integration planning, synergy tracking, and the systems, process, people, and customer workstreams needed to deliver the deal thesis.





Lead business systems implementations and transformations (e.g., CRM, ERP, finance, HR, and data platforms), including requirements alignment, vendor management, change management, and adoption.

Planning, Governance, and Execution

Define project charters, scope, success metrics, milestones, resourcing, and budgets; establish transparent ownership and decision rights across teams.

Build and run program governance, including steering committees, cadences, RAID (risks, assumptions, issues, dependencies) management, and escalation paths.

Proactively identify risks, interdependencies, and resource conflicts; drive resolution and make trade‑off recommendations to leadership.

Track and report progress, spend, and perks realization; ensure initiatives deliver their intended business outcomes, not just on‑time completion.

Stakeholder Management and Communication

Serve as a trusted partner to executives and functional leaders, providing clear, concise, and timely status, insight, and recommendations.

Influence and align stakeholders without direct authority; build momentum and resolve conflict across teams with competing priorities.

Lead change management and communications so that affected employees, customers, and partners understand and adopt new ways of working.

AI-Enabled Ways of Working and Continuous Improvement

Apply AI tools and automation to accelerate project planning,



status reporting, documentation, analysis, and knowledge capture, and share effective practices across the team.

Evaluate and help implement AI‑enabled capabilities and workflows within the initiatives they lead.

Build and continuously improve repeatable playbooks, templates, and frameworks for strategic project delivery, integration, and launch readiness.

Mentor and guide project leads and cross‑functional team members on project management best practices.

Qualifications The ideal candidate is a proven, hands‑on project and program leader who thrives in ambiguity, moves quickly, and delivers results through others. They combine strong structure and discipline with the curiosity to use AI to work smarter.

Education Bachelor's degree in Business, Operations, Engineering, Information Systems, or a related field, or equivalent practical experience. MBA or advanced degree preferred. PMP, PgMP, Agile/Scrum, or Prince2 certification preferred.

Experience Required

5–10 years of progressive experience leading complex, cross‑functional projects or programs, ideally in a software, SaaS, or technology environment.

Demonstrated success delivering at least two of the following: go‑to‑market launches, M&A; integrations, or enterprise business systems implementations.

Track record of managing multiple initiatives at once with significant budgets, executive visibility, and many stakeholders.

Strong command of project and program management methodologies (waterfall, agile, and hybrid) and tools, along with strong financial, analytical, and business acumen.

Excellent written, verbal, and executive‑level presentation skil

📌 Senior Manager, Strategic Project Management (Winnipeg)
🏢 Datasite
📍 Winnipeg