Director, Software Engineering

PointClickCare; Mississauga; On-site; CAD 211,000 - 235,000; Full time

Benefits offered by this job

Benefits starting from Day 1

Retirement Plan Matching (RRSP & 401K)

Flexible Paid Time Off

Lifestyle/Wellness Spending Account

Parental & Caregiver Leaves

Fertility & Adoption Support

Continuous Development Support Program

Employee Assistance Program

Learning Programs & Resources

Employee Recognition … and more!

Job summary

PointClickCare is seeking a Director of Software Engineering to lead the Transitions of Care engineering organization. The role reports to the VP of Engineering and oversees about 50 engineers through 10–11 managers, guiding roadmaps, architecture, and AI-enabled product scaling in a cloud-based environment.

The ideal candidate has 15+ years in software leadership, proven product collaboration, and a strong cloud/AI background.

Qualifications

• 15+ years of progressive software engineering experience with leadership in large organizations.
• Proven experience leading multiple engineering teams through several layers of management.
• Bachelor’s degree in Computer Science, Information Technology, or related field.
• Proven track record partnering with Product Management and executive stakeholders to define strategy and deliver outcomes.
• Experience defining and implementing software engineering best practices across the full SDLC.
• Strong leadership, coaching, and building high-performing teams.
• Experience delivering large-scale cloud-based solutions using Azure, AWS, and/or GCP.
• Familiarity with modern AI technologies and scaling AI-enabled products.
• Strong architectural background to guide strategic technology decisions.
• Ability to influence across engineering, product, sales, customer success, and executives.
• Excellent communication, problem-solving, organizational, and stakeholder management skills.
• Ownership mindset and urgency to deliver results.

Responsibilities

• Partner with Product Management to develop roadmaps balancing product innovation, technical investments, and platform strategy.
• Unify multiple engineering teams into a cohesive organization with clear priorities and cross-functional collaboration.
• Develop engineering strategies that ensure scalable, reliable, and secure platforms.
• Drive architectural decisions across Core and Platform Services stacks.
• Coach and develop managers to increase leadership capability and talent density.
• Evaluate and prioritize technical initiatives with clear business value.
• Lead hiring, workforce planning, and succession planning to attract top talent.
• Collaborate with engineering, product, sales, customer success, and executives to deliver large-scale initiatives.
• Champion Agile and Kanban practices and a culture of continuous improvement.
• Support scaling AI-driven products and data ecosystems across the organization.

Skills

Software engineering leadership

Cloud platforms (Azure/AWS/GCP)

AI familiarity

Engineering strategy

Stakeholder management

Mentorship & coaching

Communication

Technical architecture

Product collaboration

Agile / Kanban

Education

Bachelor’s degree in Computer Science, Information Technology, or related field

Job description

Job Title: Director, Software Engineering

Location: Remote – Canada or Hybrid – Mississauga, ON

Travel to Office expectations

For Remote Roles: If this role is remote, there will be in-office events that will require travel to and from the Mississauga and/or Salt Lake City office. These will include, but not limited to, onboarding, team events, semi-annual and annual team meetings.

For Hybrid Roles: If this role is Hybrid, there will be an expectation to reside within commutable distance to the office/location specified in the job listing. This will include, but not limited to, weekly/bi-weekly/monthly events in the office with your specific team. This is a requirement for this role.

At PointClickCare our mission is simple: to help providers deliver exceptional care. And that starts with our people. As a leading health tech company that’s founder-led and privately held, we empower our employees to push boundaries, innovate, and shape the future of healthcare.

With the largest long-term and post-acute care dataset and a Marketplace of 400+ integrated partners, our platform serves over 30,000 provider organizations, making a real difference in millions of lives. We also reinvest a significant percentage of our revenue back into research and development, ensuring our employees have the resources to innovate and make a lasting impact. Recognized by Forbes as a top private cloud company and honored as one of Canada’s Most Admired Corporate Cultures, we offer flexibility, growth opportunities, and meaningful work.

At PointClickCare, we empower our people to be the architects of a smarter healthcare future; one that is human-first and accelerated by AI to create meaningful and lasting change. Employees harness AI as a catalyst for creativity, productivity, and thoughtful decision-making. By integrating AI tools into our daily workflows, collaboration is enhanced, outcomes are improved, and every team member has the proficiency to maximize their impact. It all starts with our hiring practices where we uncover AI expertise that complements our mission, and we continue to invest in training and development to nurture innovation throughout the employee journey.

Join us in redefining healthcare — so it doesn’t just survive, it thrives. To learn more about PointClickCare, check out Life at PointClickCare and connect with us on Glassdoor and LinkedIn.

Position Summary:

The Software Engineering Director will lead the engineering organization responsible for Transitions of Care. Reporting to the VP, Engineering, this leader will oversee a team of approximately 50 engineers through a management structure of 10-11 managers and senior managers.

The Director will partner closely with Product Management to define roadmaps, align engineering strategy with business priorities, and build a cohesive, high-performing organization. This role requires a strategic engineering leader who can mentor leaders, strengthen talent density, drive technical architecture decisions, and help scale AI-powered products and platforms within a cloud-based ecosystem.

Key Responsibilities:

• Partner with Product Management to develop and execute roadmaps that balance product innovation, technical investments, operational excellence, and long-term platform strategy.
• Lead and unify multiple engineering teams into a cohesive organization, establishing clear priorities, shared objectives, and strong cross-functional collaboration.
• Develop and execute engineering strategies that support current and future business needs while ensuring scalable, reliable, and secure platform capabilities.
• Drive technical architecture decisions across Core and Application & Platform Services technology stacks, partnering with architecture and shared services teams.
• Coach, mentor, and develop managers and senior managers, building leadership capability and increasing organizational effectiveness and talent density.
• Guide teams in evaluating and prioritizing technical initiatives by clearly articulating business value and aligning investments with strategic objectives.
• Lead hiring, workforce planning, and succession planning efforts to attract, retain, and develop top engineering talent.
• Collaborate with engineering, product, sales, customer success, and executive stakeholders to successfully deliver complex, large-scale initiatives.
• Champion Agile and Kanban development methodologies and foster a culture of continuous improvement, accountability, and technical excellence.
• Support the development and scaling of AI-driven products and services, helping create an integrated data ecosystem that enables innovation across the organization.

Required Skills & Qualifications:

• 15+ years of progressive software engineering experience, including significant leadership experience within complex technology organizations.
• Proven experience leading large engineering organizations through multiple layers of management, including managers and senior managers.
• Bachelor’s degree in Computer Science, Information Technology, or a related field.
• Demonstrated success partnering with Product Management and executive stakeholders to define strategy, prioritize investments, and deliver business outcomes.
• Experience defining and implementing software engineering best practices across the full software development lifecycle.
• Strong track record of organizational leadership, including coaching leaders, driving change, and building high-performing teams.
• Experience delivering large-scale cloud-based solutions using Azure, AWS, and/or Google Cloud Platform.
• Familiarity with modern AI technologies, with preference given to candidates who have successfully built and scaled AI-enabled products or platforms.
• Strong technical architecture background with the ability to evaluate trade-offs and guide strategic technology decisions.
• Demonstrated ability to influence across engineering, product, sales, customer success, and executive teams.
• Excellent communication, problem-solving, organizational, and stakeholder management skills.
• Strong sense of ownership, urgency, accountability, and commitment to delivering results.

At PointClickCare, base salary is one of the many components that make up our total rewards package. The Canada base salary range for this position is $211,200 - $234,600+ bonus + benefits. Our salary ranges are determined by job and level. The range displayed on each job posting reflects the target for new hire salaries for the position across all Canada locations. Within the range, individual compensation is determined by job-related skills and knowledge, relevant experience including professional and lived experience, and/or work location. Your recruiter can share more information about our total rewards package during the hiring process.

PointClickCare Benefits & Perks

• Benefits starting from Day 1
• Retirement Plan Matching (RRSP & 401K)
• Flexible Paid Time Off
• Lifestyle/Wellness Spending Account
• Parental & Caregiver Leaves
• Fertility & Adoption Support
• Continuous Development Support Program
• Employee Assistance Program
• Learning Programs & Resources
• Employee Recognition … and more!

Equal Employment Opportunity:

It is the policy of PointClickCare to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. PointClickCare welcomes and encourages applications from people with disabilities. Accommodations are available upon request for candidates taking part in all aspects of the selection process. Please contact [e-mail] should you require any accommodations.

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PointClickCare is committed to Information Security. By applying to this position, if hired, you commit to following our information security policies and procedures and making every effort to secure confidential and/or sensitive information.

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