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.

• 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 Dev Ops/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.

• 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.

• 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 Dev Ex.
• Champion automation across build, test, deployment, and maintenance operations.

• 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.

• 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.

• 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 Dev Ops and CI/CD background.
• Understanding of HIPAA, FHIR, HL7, and healthcare compliance.
• Excellent leadership and communication skills.

• 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.

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  or .