Director, Software Engineering

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.

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.

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!