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 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.

Lead the end-to-end delivery of complex, large-scale ERP implementations from discovery through handover. Manage project scope, budgets, and resourcing while serving as the primary strategic partner for client executives.

Requires a degree in Business, Engineering, or Computer Science and over 10 years of experience leading complex software implementation projects. Proficiency in project management tools and experience in regulated industries or SaaS environments is highly desired.

• Flexible Hours • Remote Work • Employee Stock Option Plan • Yearly Performance Bonus • Group Health Insurance • Dental Insurance • Virtual Medicine Plans • Wellness Benefit • Computer Equipment

• Change ManagementPreferred
• Project managementPreferred
• Stakeholder ManagementPreferred

Identified from the job description. Confirm important requirements above.

• ERP Implementation
• Project Management
• Stakeholder Management
• Budget Management
• Risk Mitigation
• Executive Communication
• Waterfall Methodology
• Agile Methodology
• Hybrid Delivery
• Change Management
• SaaS Implementation
• Resource Allocation
• Project Governance
• Contract Management
• Presales Scoping
• Cross-functional Leadership

• Management & Leadership
• Software
• Technology
• Consulting
• Finance & Accounting

Minimum education

Bachelor’s degree

Minimum experience

10+ years

Apply by

Oct 4, 2026

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Montreal, Quebec, Canada

Seniority

Mid-Senior level