Director, Software Engineering

Location: Remote - US. Occasional travel to Mississauga and/or Salt Lake City offices required for onboarding, team events, and semi-annual/annual meetings.

At PointClickCare, our mission is to help providers deliver exceptional care. As a leading health tech company, we empower employees to 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. We reinvest a significant percentage of revenue into research and development, fostering a culture of flexibility, growth, and meaningful work. Recognized by Forbes as a top private cloud company and one of Canada’s Most Admired Corporate Cultures, we integrate AI tools into daily workflows to enhance collaboration, productivity, and decision-making.

About the Role

The Software Engineering Director will lead the engineering organization responsible for Transitions of Care, overseeing a team of approximately 50 engineers through a management structure of 10-11 managers and senior managers. Reporting to the VP of Engineering, this role partners closely with Product Management to define roadmaps, align engineering strategy with business priorities, and build a cohesive, high-performing organization. The ideal candidate is a strategic leader who can mentor teams, drive technical architecture decisions, and scale AI-powered products within a cloud-based ecosystem.

Responsibilities

• Partner with Product Management to develop and execute roadmaps balancing product innovation, technical investments, operational excellence, and long-term platform strategy.
• Lead and unify multiple engineering teams, establishing clear priorities, shared objectives, and strong cross-functional collaboration.
• Develop and execute engineering strategies supporting 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 to build leadership capability and increase organizational effectiveness.
• Guide teams in evaluating and prioritizing technical initiatives by articulating business value and aligning investments with strategic objectives.
• Lead hiring, workforce planning, and succession planning to attract, retain, and develop top engineering talent.
• Collaborate with engineering, product, sales, customer success, and executive stakeholders to deliver complex, large-scale initiatives.
• Champion Agile and Kanban methodologies, fostering a culture of continuous improvement, accountability, and technical excellence.
• Support the development and scaling of AI-driven products and services, creating an integrated data ecosystem for innovation.

Requirements

• 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 (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 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; preference given to candidates who have built and scaled AI-enabled products or platforms.
• Strong technical architecture background with the ability to evaluate trade-offs and guide strategic technology decisions.
• 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.

Pay

US base salary range: $217,800 - $242,000, plus bonus and benefits. Ranges are determined by job and level, with individual compensation based on skills, relevant experience, and work location.

Benefits

• Benefits starting from Day 1.
• Retirement plan matching (RRSP & 401K).
• Flexible paid time off.
• Lifestyle/wellness spending account.
• Parental and caregiver leaves.
• Fertility and adoption support.
• Continuous development support program.
• Employee assistance program.
• Learning programs and resources.
• Employee recognition programs.