Senior Project Manager

WELL Health Technologies Corp • Toronto, ON

5d • CA$105,000 - CA$135,000 • Hybrid

About The Position

The WELLSTAR Clinical Platform Group is responsible for the development and support of the EMR platforms such as OSCAR and Cerebrum, which are leading Electronic Medical Record (EMR) software's in Canada that supports thousands of providers and millions of Canadian patients across the country. Primarily located in the greater Toronto area and the greater Vancouver area, the team currently works remotely with hybrid support where desired. Reporting to the Director of Engineering, the Senior Project Manager plays a central role in driving the planning, execution, and on-time delivery of initiatives across the OSCAR team. While the role is anchored to OSCAR, this individual will partner across the broader WELLSTAR Clinical Platform Group and may take on projects shared across EMR teams. They will own project plans, timelines, scope, status reporting, dashboards, and KPIs— keeping cross-functional teams aligned and stakeholders informed from kickoff through delivery. The ideal candidate combines strong project and program management fundamentals with the ability to navigate complex, cross-functional initiatives in a regulated healthcare environment. Experience in the healthcare or EMR space is a significant asset, and technical familiarity with software delivery is a strong bonus that helps this person speak the language of engineering, QA, and infrastructure teams.

Requirements

• A proven record of delivering complex, cross-functional initiatives.
• Bring structure to ambiguity, thrive in fast-paced, mission driven environments, and take ownership of delivery from planning through close-out.
• Comfortable holding teams accountable while keeping relationships strong.
• Bring structure, clarity, and follow-through to every initiative.
• Keep teams focused on outcomes and committed dates.
• Spot risks and scope creep early and act before they become problems.
• Embrace modern AI tools to automate reporting and increase productivity while maintaining strong Agile project management fundamentals.
• Work well across engineering, product, infrastructure, and security teams.
• Adjust to shifting priorities while keeping delivery stable and predictable.
• Balance deep experience with humility, creating space for others to contribute and surfacing the best ideas without ego.
• Focused on delivering measurable business outcomes through disciplined execution.
• Able to communicate concisely and clearly in a structured, thoughtful fashion. Provides context (background) and clarity (details) as required.
• Project Management: End-to-end delivery, road mapping, planning, scheduling, scope and change management
• Agile, Scrum/Kanban, Waterfall, and PMO/governance frameworks
• Risk and issue tracking, mitigation, and executive-level escalation management
• Status reporting, KPI dashboards, and automated leadership reporting
• Experience using AI-assisted tools (e.g., Claude, ChatGPT, AI-driven reporting and analytics) to automate dashboards, status reports, and KPIs and to increase team productivity
• Stakeholder Management: Executive and cross-functional stakeholder alignment and communication
• Notion, Jira, Confluence, MS Project, Smartsheet, SharePoint, or similar
• Comfortable working with software delivery teams; understanding of release management, and the software development lifecycle is a strong bonus
• 8+ years managing complex, cross-functional software or technology projects, ideally including concurrent portfolios

Nice To Haves

• Experience in healthcare or EMR/EHR space
• PMP, PMI-PBA, PMI-ACP, or equivalent project management certification
• Familiarity with healthcare standards and compliance frameworks (e.g., HL7/FHIR, PHIPA, SOC2, ISO27001)
• Experience managing regulatory or compliance-driven programs
• Background working with technical teams

Responsibilities

• Build and maintain detailed project plans, roadmaps, and timelines across OSCAR initiatives.
• Coordinate dependencies across teams, sequence work effectively, and drive initiatives from kickoff to delivery—consistently meeting committed dates and quality bars.
• Define and protect project scope.
• Proactively identify scope creep, manage change requests through a clear process, and renegotiate timelines or trade-offs transparently with stakeholders to keep delivery realistic and profitable.
• Establish clear, consistent status reporting across initiatives.
• Act as the primary liaison between leadership, product, engineering, and stakeholders—ensuring everyone is aligned on priorities, timelines, risks, and delivery expectations.
• Design and maintain dashboards and KPI reporting that give leadership real-time visibility into delivery health.
• Automate reporting where possible to reduce manual effort and surface risks early.
• Proactively apply AI-assisted tools to boost personal and team productivity and to automate the production of dashboards, status reports, and KPIs.
• Use AI to draft and summarize status updates, compile cross-team reporting, generate and refresh delivery dashboards, surface risks and trends from project data, and reduce manual reporting toil—so the team spends less time assembling updates and more time delivering.
• Establish lightweight, repeatable AI-assisted workflows that keep reporting consistent, accurate, and timely while maintaining strong project management fundamentals.
• Run effective agile ceremonies such as daily standups, planning, retrospectives, and reviews.
• Keep ceremonies focused and time-boxed, remove blockers raised by the team, and ensure work is well-defined, prioritized, and flowing.
• Tailor agile practices to each team's needs and reinforces healthy habits that improve velocity and predictability.
• Maintain risk and issue logs, identify risks early, and drive mitigation.
• Step into at-risk projects to stabilize delivery, realign timelines, and rebuild stakeholder trust before issues escalate.
• Manage relationships across internal teams and external stakeholders.
• Run effective meetings, set clear expectations, and ensure alignment on priorities and outcomes across OSCAR and, where applicable, other EMR teams.
• Strengthen and standardize project management practices across the EMR group.
• Introduce repeatable templates, governance artifacts, and lightweight processes that improve delivery predictability without slowing teams down.
• Champion cross-team collaboration.
• Maintain clear, accessible project documentation, charters, plans, decisions, and retrospectives, so knowledge is shared, and delivery practices are scalable across teams.

Benefits

• Competitive salary that reflects the value and expertise of the successful candidate
• Great Place to Work® certified workplace culture rooted in trust, inclusivity, and employee well-being

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed