About the role

Head of Product and Engineering leading ProgressionLIVE’s web and mobile field-service software. Owning product strategy, engineering execution, technical architecture, and AI-powered customer value.

Responsibilities

Own product and technical roadmaps aligned with company strategy.
Lead engineering execution, team culture, and the transition from ticket execution to problem-solving and impact measurement.
Maintain technical depth through code review, code contributions, prototyping, debugging, investigation, and architectural guidance.
Guide the technical direction of the Java/Spring backend, Vue 3/TypeScript web application, and mobile application.
Ensure the reliability, security, maintainability, and scalability of the multi-tenant SaaS platform.
Lead ProgressionLIVE’s AI strategy for development productivity and differentiated customer value.
Establish responsible AI-use standards and prototype high-impact agentic workflows and internal tools.
Define product strategy through customer discovery, evidence-based prioritization, prototypes, and incremental releases.
Balance new development, platform improvements, technical debt, reliability, security, and customer outcomes.
Establish modern engineering practices, ownership processes, monitoring, on-call, incident response, and operational metrics.
Recruit, coach, and develop a high-performing product and engineering team.
Work closely with the GM and cross-functional leaders on product and technical decisions.

8+ years of software development leadership experience, including building and scaling engineering teams, or equivalent experience as a founder/CTO.
Proven experience as a senior product or engineering leader with accountability for business outcomes.
Strong technical foundation and the ability to maintain credibility with engineering teams and guide architectural decisions.
Deep product judgment: define strategy, investigate customer problems, prioritize investments, measure impact, and iterate.
Track record of leading organizational change, including process, culture, or technical transformation at scale.
Executive communication and cross-functional leadership across product, engineering, sales, and customer success.
Ability to hire, coach, and scale high-performing technical teams and build organizational capability over time.
Strategic thinking: balance innovation, technical debt, reliability, security, and business needs.
Customer empathy: deep understanding of how customers work and a willingness to challenge solutions that lack customer evidence.
Practical experience with modern development practices and AI-assisted workflows, with enthusiasm for continuous modernization.
Technical depth with Java, Spring, Hibernate, Vue 3, TypeScript, mobile applications, AWS, GitHub Actions, and Terraform, or the ability to understand unfamiliar production systems and guide sound technical decisions.

4-day workweek
Remote work
Group insurance after 3 months (50% paid by the company; family coverage available)
Employee Assistance Program (EAP)
Corporate wellness program
Group RRSP (RPDB)
3 weeks of vacation from day one (available after 3 months)
Regular social and sports activities
Annual training budget
Annual personal budget for sports or remote-work equipment
Coffee, snacks, and good vibes guaranteed at the office