Job Description:Vice President of EngineeringOverview- 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
