Senior Director of Engineering

Job Description:

Senior Director of Engineering – Healthcare AI & Innovation

Overview

• We are seeking a visionary Senior Director of Engineering to lead our R&D and software engineering teams as we build AI-enhanced healthcare solutions. This role requires a strategic, hands-on engineering leader with deep experience in intelligent automation, and managing distributed engineering organizations. You will be responsible for elevating engineering excellence, driving AI-first innovation, and enabling measurable improvements in productivity and product quality.

Strategic Technology Leadership

• Define and execute an engineering strategy aligned with our AI-first, automation-focused healthcare mission.
• Lead multi-disciplinary teams across application engineering, R&D/AI innovation, and DevOps/infra.
• Drive modernization and innovation within a .NET, C#, React, Oracle-based architecture.
• Partner with Product leadership to translate roadmap priorities into scalable, maintainable engineering plans.
• Build a long-term technology vision focused on reliability, usability, and intelligent automation.

AI, Automation & R&D Innovation

• Lead R&D initiatives for AI-driven insights, workflow automation, decision support, and productivity tools.
• Oversee prototyping, experimentation, and rapid iteration for AI-enhanced features.
• Guide integration of AI/ML capabilities into the product in partnership with Product.
• Support model operationalization using practical, lightweight deploy/monitor frameworks.
• Ensure AI capabilities meet healthcare requirements around accuracy, auditability, privacy, and compliance.

Engineering Operations & Metrics

• Implement engineering KPIs: velocity, cycle time, defect rate, MTTR, release stability, and code quality.
• Build dashboards to track engineering productivity, release predictability, and quality trends.
• Drive improvements in CI/CD automation, test automation, environment consistency, and DevEx.
• Champion automation across build, test, deployment, and maintenance operations.

Architecture, Software Quality & Reliability

• Set high standards for code quality, maintainability, performance, and test coverage.
• Strengthen architectural governance within a monolithic or modular .NET architecture.
• Drive modernization and technical debt reduction.
• Ensure secure and compliant development aligned with HIPAA, SOC 2, and healthcare data standards.

Distributed Team Leadership & Culture

• Build and inspire distributed engineering teams across time zones.
• Promote collaboration, async communication, and strong remote culture.
• Mentor engineering leaders and grow a robust succession pipeline.
• Foster psychological safety, innovation, diversity, and execution excellence.

Qualifications

• 12+ years software engineering experience; 7+ years leading engineering organizations.
• Deep experience with .NET, C#, React, and enterprise relational databases (Oracle preferred).
• Strong ability to lead teams in an enterprise architecture.
• Experience integrating AI/ML and automation into production systems.
• Strong DevOps and CI/CD background.
• Understanding of HIPAA, FHIR, HL7, and healthcare compliance.
• Excellent leadership and communication skills.

Success Indicators

• Improved engineering velocity, predictability, and release quality.
• Delivery of AI- and automation-driven capabilities.
• Increased automation and reduced manual overhead.
• Higher team engagement
• Reduced technical debt and stronger system reliability.
• A forward-looking technology roadmap aligned with company goals.

Business Unit:

Computrition - Canada

Scheduled Weekly Hours:

37.5

Number of Openings Available:

1

Worker Type:

Regular

More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.

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