Job Description:Vice President of EngineeringBuild Technology That Matters.As part of Constellation Software Inc. (TSX: CSU), Computrition combines the stability of an established market leader with the opportunity to shape the next generation of enterprise software. We're investing in modern technologies, AI-enabled engineering practices, and innovative product capabilities that help customers solve increasingly complex operational challenges.
We invest in our people and foster a culture of collaboration, accountability, continuous learning, and professional growth where employees can make a meaningful impact. You'll join experienced professionals who are passionate about solving meaningful problems and delivering measurable customer outcomes.
If you're looking to build technology that matters while growing your career with a stable, innovative company, we'd like to hear from you.
Overview- We're hiring a Vice President of Engineering to lead our core engineering organization, including R&D and application engineering, while partnering closely with QA, Release Management, and DevOps leadership to strengthen engineering estimation, quality, delivery predictability, automation, and operational excellence across the software delivery lifecycle.
- Reporting directly to the CTO, you will be accountable for engineering execution, software quality, delivery predictability, operational excellence, engineering estimation excellence, and the continued evolution of our AI-enabled Software Development Lifecycle (AI-DLC).
- Success requires close partnership with Product, Sales, Professional Services, Customer Success, Support, Marketing, and executive leadership to ensure Engineering consistently delivers solutions that meet customer needs and business objectives.
- Success will be measured by your ability to build a disciplined, highly predictable engineering organization that consistently delivers exceptional software quality, enables AI-enhanced product capabilities that create customer value, continually improves engineering estimation accuracy and delivery predictability, and earns the confidence of customers, colleagues, and executive leadership through consistent execution.
- This is a fully remote position open to candidates located in the United States or Canada. Occasional travel is required for leadership meetings, customer engagements, and company events.
Strategic Technology Leadership- Lead Engineering as a single accountable organization spanning application engineering, R&D, quality engineering, release management, and DevOps/Infrastructure.
- Support the CTO in shaping the company's long-term technology vision while owning and executing the engineering strategy required to deliver that vision through disciplined execution, operational excellence, continuous improvement, and measurable business outcomes.
- Drive modernization of our enterprise technology platform-anchored in .NET, C#, React, Oracle, DevOps, CI/CD, and modern engineering practices-to improve scalability, reliability, security, developer productivity, and delivery predictability.
- Partner with Product leadership to translate product vision into executable engineering roadmaps, resource plans, delivery commitments, and high-quality customer outcomes.
- Develop and execute multi-year engineering investment plans that improve software quality, developer productivity, platform reliability, operational excellence, and business outcomes.
AI-Enabled Engineering & Product Delivery- Lead implementation and continuous improvement of our AI-enabled Software Development Lifecycle (AI-DLC), embedding AI throughout the engineering lifecycle to improve software quality, developer effectiveness, and engineering efficiency.
- Lead engineering execution of AI-enhanced capabilities across our enterprise software platform, ensuring practical customer value within our on-premises solutions while supporting broader strategic technology initiatives led by the CTO.
- Establish engineering standards, governance, review practices, and quality controls that ensure AI-assisted development meets enterprise standards for quality, security, compliance, and maintainability.
- Ensure AI capabilities-both customer-facing and internal-meet healthcare requirements for accuracy, auditability, privacy, security, and regulatory compliance.
- Develop engineering leaders capable of driving organizational excellence, innovation, continuous improvement, and effective adoption of AI-enabled engineering practices.
Engineering Execution, Estimation & Delivery Excellence- Own engineering execution from concept through customer delivery, ensuring solutions are appropriately estimated, staffed, architected, developed, tested, released, and supported with first-time quality.
- Establish industry-leading engineering estimation, capacity planning, and delivery forecasting disciplines that enable confident customer commitments, predictable execution, and measurable improvements in estimation accuracy over time.
- Continuously improve engineering estimation accuracy, forecasting precision, resource planning, engineering productivity, and delivery performance through disciplined operating practices and data-driven decision making.
- Build an engineering organization that consistently delivers high-quality software on predictable schedules and within planned resource commitments.
- Create a culture where first-time quality is achieved through disciplined architecture, testing, automation, and engineering excellence.
Customer Value & Business Impact- Partner with Product, Sales, Professional Services, Customer Success, Support, Marketing, and executive leadership to ensure engineering priorities remain aligned with customer needs and business objectives.
- Actively participate in strategic customer engagements to understand operational challenges firsthand and translate customer feedback into scalable product capabilities.
- Ensure engineering teams understand the customer and business outcomes their work enables.
- Balance customer commitments, platform reliability, engineering capacity, technical debt, and long-term technology investments to maximize customer and business value.
Engineering Operations- Own engineering KPIs including engineering estimation accuracy, delivery predictability, engineering velocity, cycle time, defect rates, MTTR, release stability, code quality, and engineering productivity.
- Develop executive dashboards providing transparent insight into engineering performance, forecasting accuracy, quality, productivity, and organizational health.
- Continue advancing CI/CD, automated testing, release automation, developer experience, engineering tooling, and AI-assisted engineering workflows to improve engineering efficiency and delivery quality.
- Champion automation wherever it creates measurable business value.
- Build repeatable engineering processes that scale with organizational growth.
Architecture, Quality & Reliability- Establish high standards for software quality, maintainability, performance, security, architectural consistency, and AI-assisted software development.
- Partner with Product leadership and the CTO to ensure engineering execution aligns with product strategy, architectural standards, platform evolution, and long-term technology direction.
- Manage technical debt as a strategic investment portfolio, making deliberate investment decisions.
- Ensure engineering practices consistently satisfy HIPAA, SOC 2, healthcare security standards, and enterprise software best practices.
Organization & Leadership- Build, mentor, and develop a high-performing distributed engineering organization.
- Develop engineering leaders capable of making sound technical and business decisions independently and collaboratively.
- Foster a culture of accountability, collaboration, continuous learning, innovation, execution excellence, and continuous improvement.
- Partner across Product, Sales, Professional Services, Customer Success, Support, Marketing, and executive leadership to solve enterprise-wide challenges, align priorities, and ensure coordinated execution across the customer lifecycle.
- Serve as a trusted advisor to the CTO by contributing to the evolution of engineering capabilities, organizational maturity, and long-term technology leadership.
- Represent Engineering confidently with executive leadership, customers, and strategic partners.
Qualifications- 12+ years of progressive software engineering experience, including at least 7 years leading engineering organizations of increasing scope and responsibility.
- Demonstrated success leading engineering organizations responsible for mission-critical enterprise software.
- Experience owning engineering operating budgets, workforce planning, vendor management, and engineering investment prioritization.
- Deep technical credibility across Microsoft enterprise technologies including .NET, C#, React, and Oracle.
- Demonstrated hands-on leadership implementing AI-enabled Software Development Lifecycle (AI-DLC) or comparable AI-augmented software engineering practices.
- Experience integrating AI/ML and intelligent automation into enterprise software products and engineering operations.
- Demonstrated success improving engineering estimation, capacity planning, delivery forecasting, execution predictability, and engineering operating disciplines.
- Demonstrated success establishing engineering operating metrics, executive dashboards, and performance measures that improve predictability, transparency, and accountability.
- Strong background in DevOps, CI/CD, quality engineering, release management, and engineering automation.
- Experience operating engineering organizations within SOC 2, HIPAA, and other regulated software environments. Familiarity with FHIR and HL7 is preferred.
- Excellent communication and executive presentation skills.
- Demonstrated ability to operate as an executive business partner, contributing beyond Engineering to broader technology strategy, business strategy, commercial outcomes, and customer success.
Success in This Role- Built a highly predictable engineering organization trusted by executive leadership and cross-functional partners.
- Delivered measurable improvements in engineering estimation accuracy, delivery predictability, engineering velocity, release quality, and overall engineering productivity.
- Successfully expanded AI-enabled engineering practices while delivering AI-enhanced capabilities across our enterprise software platform that create measurable customer value.
- Reduced manual engineering effort through increased automation while maintaining exceptional quality, reliability, and regulatory compliance.
- Built a strong engineering leadership bench capable of scaling with the organization.
Established Engineering as a disciplined, high-performing organization that serves as a trusted execution partner to the CTO and executive leadership while enabling innovation, commercial success, customer satisfaction, and long-term business growth
Business Unit:Computrition - Canada
Scheduled Weekly Hours:37.5
Number of Openings Available:1
Worker Type:Regular
