Senior Project Manager (Enterprise)

About the role:

We're looking for a senior project manager to own enterprise implementation programs end to end and to serve as the senior point of contact for client executives throughout. You'll coordinate stakeholders, manage the commercial side of each engagement, and run the governance that keeps projects on track. You'll also partner with Product, Engineering and Sales on complex opportunities so that what we commit to is feasible and grounded in what comparable programs actually cost. This is a build role: you'll create the project management practices, standards and tooling that delivery runs on.

What you can expect:

Delivery Ownership

- Own end-to-end delivery of enterprise implementation programs, including scope, schedule, budget, resourcing and risk
- Manage the full onboarding lifecycle — discovery, requirements, configuration and UAT — through to handover
- Maintain requirements traceability from signed scope through build to UAT sign-off
- Structure large scopes into independently deliverable phases, each with its own UAT and go-live

Client and Executive Engagement

- Serve as the senior point of contact for client executives and sponsors, owning expectations and communication cadence
- Distinguish client-requested timelines from Estateably's committed dates, and manage the gap transparently with both sides
- Prepare and deliver executive-level presentations — steering committee updates, program health reviews and C-suite briefings — translating delivery detail into decisions and recommendations

Cross-Functional and Partner Coordination

- Coordinate BAs, PMs, developers, QA and Support to deliver on time, on budget and on scope, partnering closely with Business Analysts to align solution design with delivery feasibility
- Manage dependencies across the client's technology partners and incumbent providers, including engagements where a third party's schedule governs overall program timelines

Commercial and Financial Management

- Manage project financials: budgeting, time accounting, forecasting and change order management
- Own contracts and statements of work across the engagement




- Reconcile actuals against original estimates and feed corrected assumptions back into the estimating model for future scopes

Governance, Risk and Escalation

- Facilitate project governance: steering committee meetings, status reporting and stage-gate reviews
- Enforce stage gates, ensuring work does not advance until exit criteria are met
- Identify, track and mitigate project risks and issues, escalating appropriately and driving resolution to closure

Technical Sales and Solution Shaping

- Define how solutions are presented in technical sales, including what is committed to and the evidence supporting it
- Partner with Product and Engineering on complex opportunities to validate feasibility, sequencing and effort before Estateably commits
- Steer complex scopes toward core product capability rather than client-specific build, and identify functionality that should be productized from existing work
- Bring delivery data into pursuit: actual cost of comparable programs, variance in prior estimates, and the implications for current pricing

Practice and Process Ownership

- Create and implement Estateably's project management practices: methodology, templates, estimating standards, gates and reporting
- Select and stand up the tooling behind them for time accounting, resourcing, budget, forecasting and project financials
- Drive adoption of the practices and tooling across the organization.

What we're looking for:

- Degree in Business, Engineering, Computer Science, or a related field
- 10+ years leading large-scale, complex software implementation programs, including technology, transformation, or business process initiatives
- 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
- Demonstrated ownership of project commercials: budgets, forecasting, SOWs, change orders,



and estimate-to-actual reconciliation
- Experience establishing project management standards, methodology or tooling, not only operating within an existing framework
- A collaborative approach and a track record of building client trust through transparency and professionalism
- Experience selecting or implementing project management tooling (Jira, MS Project, Smartsheet or equivalent)
- Experience supporting presales or solution scoping alongside Product and Engineering
- 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.
- Robust 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.

📌 Senior Project Manager (Canada)
🏢 Estateably
📍 Canada