Head of Engineering
Stay22Montreal, Quebec, Canada
Posted April 1, 2026
Full Time
About the Company
Stay22 is a leading affiliate platform that empowers media publishers, content creators, and eventâticketing partners to monetize travel and accommodation content without owning real estate. Leveraging AIâdriven conversion technology, the platform delivers seamless booking experiences that generate incremental revenue for publishers. With a global reach of over 1âŻbillion users and more than $500âŻmillion in bookings facilitated in 2024, Stay22 has established itself as a trusted partner for travelâfocused organizations. Its suite of servicesâincluding travel, accommodation, hotels, maps, and transportationâprovides endâtoâend solutions that scale with publishersâ audiences.
Job Description
Stay22 is seeking a Head of Engineering to lead and scale our engineering organization as we enter our next phase of growth. This is a senior leadership role responsible for shaping our technical vision, engineering strategy, and execution across multiple squads, while maintaining strong technical credibility with the team.
Requirements
- 15+ years of experience in software engineering
- 5+ years of experience in engineering leadership
- Proven experience operating in startup or scale-up environments
- Track record as Head of Engineering / VP Engineering in a B2B SaaS, marketplace, or ad/affiliateâdriven environment
- Strong technical background in modern backend systems, including JavaScript/TypeScript, Node.js, and Python
- Experience working with cloud platforms (GCP preferred) and scalable distributed architectures
- Strong familiarity with AI/ML systems and modern LLM tools
- Demonstrated ability to review architecture, guide technical decisions, and maintain credibility with senior engineers and staff-level developers
- Experience defining and tracking engineering performance metrics (e.g., DORA metrics) and driving operational improvements
- Strong cross-functional leadership skills, with the ability to collaborate effectively with Product, Data, and business leadership
Benefits
- Comprehensive benefits
- Flexible work schedule
- Health & dental benefits
- Retirement plans
- Learning & development opportunities
- Social & team-building activities
- Exciting retreats
