Senior Project Manager in Winnipeg

As a Senior Project Manager on our Enterprise team, you'll lead the delivery of our most complex, large-scale ERP implementations from discovery through to successful handover. You'll own scope, schedule, budget, and resourcing, serve as the trusted senior partner to client executives, and set the standard for how cross-functional delivery is run across the organization.

What you can expect:

• Own end-to-end delivery for large-scale ERP implementation projects, including scope, schedule, budget, resourcing, and risk management.
• Manage the full onboarding project lifecycle, ensuring discovery, requirements, configuration, and UAT follow best practice through to handover.
• Serve as the senior point of contact for client executives and sponsors, managing expectations, communication cadence, and executive-level reporting.
• Prepare and deliver executive-level presentations — steering committee updates, program health reviews, and C-suite briefings — translating delivery detail into clear decisions and recommendations.
• Coordinate cross-functional teams (Business Analysts, Product Managers, Developers, QA, Support) to deliver on time, on budget, and on scope.
• Partner with Business Analysts to align solution feasibility with execution.
• Identify, track, and mitigate project risks and issues, escalating appropriately and driving resolution.
• Manage project financials, including budgeting, time accounting, forecasting, and change order management.
• Facilitate project governance, including steering committee meetings, status reporting, and stage-gate reviews.
• Exercise autonomy over prioritization, sequencing, and client engagement approaches, escalating strategic or scope-altering risks as needed.
• Manage contracts and statements of work across the engagement.
• Drive continuous improvement of project management practices, tools, and templates across the organization.
• Contribute to presales activities, including scoping, estimating, and statement-of-work development.

What we're looking for:

• Degree in Business, Engineering, Computer Science, or a related field.
• 10+ years leading large-scale complex software implementation projects.
• Expertise across waterfall, agile, and hybrid delivery methodologies.
• Proven ability to manage multiple concurrent, complex projects and competing priorities.
• Strong stakeholder management and executive communication skills, both written and verbal.
• Hands-on experience managing project budgets, timelines, and resource allocation.
• Experience managing technology, transformation, software implementation, business process, or operational improvement projects.
• A collaborative approach and a track record of building client trust through transparency and professionalism.
• Project management software knowledge, such as Jira, MS Project, or Smartsheet.
• Experience with SaaS / cloud-native software implementations.
• Experience with change management practices.
• Experience in regulated industries (financial services, legal, or trust companies).
• PMP certification will be considered an asset.

Why Estateably:

• We're tackling one of the largest wealth transfers in history, in an industry overdue for transformation.
• Since launching in 2021, we’ve become the fastest-growing estate and trust platform in North America, serving 1,000+ firms across Canada and the U.S.
• Our platform helps fiduciaries handle complex, sensitive workflows that directly affect professionals and their practices.
• We’re not here to make small improvements—we’re rethinking how the industry works from the ground up.

What our team has in common:

• A hunger to learn fast and continuously.
• High ownership and accountability for results.
• A can-do, solution-oriented mindset.
• Strong collaboration skills and a team-first attitude.
• Comfort with change and fast-paced environments.

Perks & Benefits:

• Flexible hours & remote work.
• Participation in our company's Employee Stock Option Plan.
• Yearly bonus based on performance.
• Full participation in our company’s group health, dental, and virtual medicine plans.
• Wellness Benefit.
• Computer equipment.

Please note that this is a 12-month employment term, with the possibility of extension at the company's discretion. Proficiency in English is required for this role due to regular collaboration with clients and internal team members across Canada and the U.S.