Senior Project Manager

Senior Project Manager (Enterprise)
About the role:
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 managementManage the full onboarding project lifecycle, ensuring discovery, requirements, configuration, and UAT follow best practice through to handoverServe as the senior point of contact for client executives and sponsors, managing expectations, communication cadence, and executive-level reportingPrepare and deliver executive-level presentations — steering committee updates, program health reviews, and C-suite briefings — translating delivery detail into clear decisions and recommendationsCoordinate cross-functional teams (Business Analysts, Product Managers, Developers, QA, Support) to deliver on time, on budget, and on scopePartner with Business Analysts to align solution feasibility with executionIdentify, track, and mitigate project risks and issues, escalating appropriately and driving resolutionManage project financials, including budgeting, time accounting, forecasting, and change order managementFacilitate project governance, including steering committee meetings, status reporting, and stage-gate reviewsExercise autonomy over prioritization, sequencing, and client engagement approaches, escalating strategic or scope-altering risks as neededManage contracts and statements of work across the engagementDrive continuous improvement of project management practices, tools, and templates across the organizationContribute to presales activities, including scoping, estimating, and statement-of-work developmentWhat we're looking for:
Degree in Business, Engineering, Computer Science, or a related field10+ years leading large-scale complex software implementation projectsExpertise across waterfall, agile, and hybrid delivery methodologiesProven ability to manage multiple concurrent, complex projects and competing prioritiesStrong stakeholder management and executive communication skills, both written and verbalHands-on experience managing project budgets, timelines, and resource allocationExperience managing technology, transformation, software implementation, business process, or operational improvement projectsA collaborative approach and a track record of building client trust through transparency and professionalismProject management software knowledge, such as Jira, MS Project, or SmartsheetExperience with SaaS / cloud-native software implementationsExperience with change management practicesExperience in regulated industries (financial services, legal, or trust companies)PMP certification will be considered an assetWhy Estateably:
Over the next 25 years, more than $60 trillion will be transferred between generations, yet professionals and the families they serve are wholly underserved in their tools to navigate the estate and trust administration process. Estateably was founded to change that.Here’s why you’ll want to be part of it:
Massive market opportunity:
We're tackling one of the largest wealth transfers in history, in an industry overdue for transformation.Rapid growth and adoption:
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.Real problems, real impact:
Our platform helps fiduciaries handle complex, sensitive workflows that directly affect professionals and their practices.Bold, ambitious vision:
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.
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