Senior Director of Engineering

Overview Senior Director of Engineering: lead R&D and software engineering teams to build AI-enhanced healthcare solutions. A strategic, hands-on engineering leader with deep experience in intelligent automation and managing distributed engineering organizations. 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 an 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. About Jonas Software Jonas Software is a leading provider of enterprise management software solutions, serving various vertical markets including hospitality, healthcare, construction, education, personal care, and more.

We are a 100% owned subsidiary of Constellation Software Inc. and part of the CSI group of companies. Jonas Software is an Equal Opportunity Employer. If you need accommodation for a disability at any stage of the application process or want more information on our accommodation policies, contact recruitment at [email protected] or 905-470-4600. #J-18808-Ljbffr