Who you are

- 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

- 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

- Solid sense of ownership, urgency, accountability, and commitment to delivering results

What the job involves

- 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

- 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

📌 Director of Software Engineering (Toronto)
🏢 PointClickCare
📍 Toronto