Head of Product and Engineering

ProgressionLIVE develops web and mobile software for field service operations management. Used by hundreds of Canadian organizations in the CVC, plumbing, electrical, construction, transportation, and maintenance sectors.

The Role

ProgressionLIVE is seeking a Head of Product and Engineering, an operational technical leadership position reporting to the CEO. You will be responsible for product and technical roadmaps, engineering execution, and team culture. Your mandate: create a highly performing organization that balances technical excellence with customer and business results, evolving the team from ticket execution to problem-solving and impact measurement.

This requires strong software development experience and current technical expertise to review code, contribute to production, debug complex issues, and guide architecture, although you do not carry the workload of features as an individual contributor. Direct technical work should focus on high-impact and foundational efforts while strengthening team capabilities.

You will also lead ProgressionLIVE's AI strategy along two dimensions: improving product development productivity and creating AI-driven differentiated customer value.

Product Vision, Customer Discovery, and Execution

• Own the roadmap aligned with the company's strategy by developing a deep understanding of customers and gathering consistent insights from customers, sales, support, and usage data.
• Translate business objectives, customer issues, market opportunities, and technical constraints into evidence-based priorities; distinguish strategic opportunities from feature requests.
• Maintain direct contact with customers and involve developers in discovery and validation through conversations, prototypes, and incremental releases.
• Define customer and business outcomes before engaging resources; ensure teams understand the problem and desired outcomes, not just the requested features.
• Balance new development, platform improvements, technical debt, reliability, and security.
• Foster healthy collaboration between product, engineering, and customer service teams without letting the roadmap become an unranked wishlist.
• Measure adoption and impact post-launch to guide decisions.

Technical Leadership and Architecture

• Stay close to the codebase through code review, contribution, and investigation; earn the trust of the engineering team with solid technical judgment.
• Contribute code, create prototypes, and pair with developers on challenging or foundational work when it materially improves outcomes.
• Take and explain architectural trade-offs, when to refactor, when to deploy, and when additional complexity is justified.
• Guide the evolution of the Java/Spring backend and Vue 3/TypeScript web application; own the technical direction of mobile applications (offline operation, synchronization, versioning, compatibility).
• Ensure the reliability, security, maintainability, and scalability of the multi-tenant SaaS platform.
• Systematically address technical debt and platform risks while keeping modernization efforts connected to customer value.
• Develop technical leaders so architectural decisions do not solely depend on you.

AI, Developer Productivity, and Product Innovation

• Define and lead an AI-powered operational model for product and engineering. Enable developers, QA, and DevOps to effectively use AI throughout the development lifecycle, from research and specifications to implementation, testing, code review, documentation, debugging, deployment, and incident response.
• Identify and automate repetitive or low-value-add activities. Prototype high-impact agentic workflows and internal tools, evaluating them based on measurable improvements in delivery speed, quality, reliability, and team capacity, not just adoption rates.
• Establish best practices for responsible AI use (security, privacy, intellectual property, quality, accountability). Foster an experimentation culture while ensuring people remain accountable for accuracy and safety.
• Identify customer-oriented AI opportunities that create significant and differentiated value, distinguishing genuine capabilities from novelty-driven features. Partner with customers and the team to validate and prioritize.

Engineering Execution and Operational Excellence

• Establish and maintain modern engineering practices and operational excellence.
• Establish clear ownership and processes that balance delivery velocity, software quality, customer learning, and the long-term health of the platform.
• Improve delivery predictability by shortening the gap between identifying customer issues and validating solutions.
• Manage the platform's security posture, including tenant isolation, dependency management, application security, and access controls.
• Build healthy monitoring, on-call, and incident response practices; ensure production reliability remains central as delivery velocity increases.
• Track targeted metrics: availability, performance, reliability, defect rates, time to production, deployment frequency, technical debt, security, and customer impact.

Team and Organizational Leadership

• Recruit, mentor, and develop a highly performing product and engineering team with clear technical and product standards, fostering a culture of craftsmanship, curiosity, accountability, and continuous improvement.
• Evolve the organization from ticket-based execution to customer and business outcome ownership.
• Give developers customer context and exposure to exercise good judgment; set clear expectations while providing appropriate autonomy.
• Develop technical and product leaders who operate independently rather than routing decisions through you.
• Collaborate closely with the CEO and cross-functional leaders when product or technical decisions affect customers and company priorities.
• Technological Environment
• Our current environment includes:
• Java, Spring, and Hibernate
• Vue 3 and TypeScript
• Mobile applications with offline operation and synchronization requirements
• AWS, including Elastic Beanstalk, EKS, Aurora MySQL, S3, SES, and IAM
• GitHub Actions
• Terraform
• A multi-tenant SaaS architecture

You do not need to have worked with every technology we use. However, you must have the technical depth to understand an unfamiliar production system, ask solid questions, evaluate trade-offs, contribute directly if appropriate, and guide experienced developers toward healthy decisions.

Requirements

• 8+ years of leadership in software development, including building and scaling engineering teams; or equivalent as a founder/CTO.
• Proven experience as a senior product or engineering leader with responsibility for business outcomes.
• Strong technical background and ability to maintain credibility with engineering teams and guide architectural decisions.
• Deep product judgment: define strategy, investigate customer issues, prioritize investments, measure impact, and iterate.
• Background in organizational change leadership: large-scale process, culture, or technical transformation.
• Executive communication and cross-functional leadership between product, engineering, sales, and customer success.
• Ability to recruit, mentor, and grow highly performing technical teams; strengthen organizational capabilities over time.
• Strategic thinking: balance innovation, technical debt, reliability, security, and business needs.
• Customer empathy: understanding of customer needs and pain points.