Impress employers and recruiters.
Choose from hundreds of resume examples.

Target Resume Now

About the Role

The Senior Project Manager plays a central role in driving the planning, execution, and on-time delivery of initiatives across the OSCAR team. 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.

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.
Manage change requests through a clear process, and renegotiate timelines or trade-offs transparently with stakeholders.
Establish clear, consistent status reporting across initiatives.
Act as the primary liaison between leadership, product, engineering, and stakeholders.
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.
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.

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

Skills

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

Location

Toronto, ON

Work Type

Full Time
Remote
Hybrid

Experience Level

Senior
8+ years managing complex, cross-functional software or technology projects

Salary/Compensations

$105,000 - $135,000

About the Company

WELLSTAR is a leading healthcare technology and provider-solutions organization focused on empowering healthcare practitioners, clinics, and health systems through innovative software, digital health, and operational solutions.
As a technology platform, WELLSTAR brings together a growing ecosystem of healthcare products and services, including Electronic Medical Records, patient engagement tools, revenue cycle management, billing and back-office solutions, healthcare IT services, and emerging AI-enabled capabilities.
Through its portfolio of trusted healthcare technology brands, WELLSTAR supports thousands of providers and clinics across Canada and plays an important role in improving the way care is delivered, managed, and experienced.
WELLSTAR’s mission is to help healthcare organizations operate more efficiently, improve provider and patient experiences, and scale technology-enabled solutions that support better health outcomes.
The organization combines deep healthcare expertise with a collaborative, entrepreneurial approach to building practical solutions for the evolving needs of Canadian healthcare.
WELL is committed to fostering a diverse, inclusive, and accessible workplace.
WELL has been independently certified as a Great Place to Work® by the Great Place to Work Institute® Canada.
Want Read more about us: https://stories.well.company/

Equal Opportunity

WELL is committed to fostering a diverse, inclusive, and accessible workplace. We welcome and celebrate the diversity of applicants and team members across ability, race, gender identity, sexual orientation, and lived experience. We strive to create an environment where differences are valued and contribute to our collective success – this is the WELL Way.