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 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:
- 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.