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Stay22, based in Montreal, is a monetization platform helping ambitious creators and high-intent digital platforms transform existing traffic into additional revenue. The company serves over 6,500 creators and platforms with more than $1 billion in annual transactions, expanding beyond travel into retail, lifestyle, publishing, events, and transportation.
We are seeking a Director of Engineering to lead and scale our engineering organization as we enter our next growth phase. This senior leadership role reports directly to the CTO and oversees an engineering organization of approximately 40 engineers organized into multiple squads, managing a small group of Engineering Managers and senior technical leaders.
Key Responsibilities:
Engineering Leadership & Team Development
- Lead and evolve a high-performing engineering organization of ~40 engineers across multiple squads with clear expectations for quality, ownership, collaboration, and execution speed
- Evolve the engineering organization structure (squads, platform vs. product, Engineering Manager layer, Tech Leads, Staff/Principal roles) as the company scales
- Own engineering hiring standards, particularly for senior roles
- Establish robust performance, feedback, and career development processes that are fair, transparent, and aligned with company values
- Manage misalignment and underperformance at all levels with clarity and empathy
- Develop strong engineering management practices including performance calibration, career development frameworks, and mentoring of technical leaders
- Foster a culture of ownership, technical excellence, and continuous improvement
- Build succession planning for critical roles (Tech Leads, Engineering Managers, Staff Engineers)
- Establish clear career ladders and levels for individual contributors and managers in partnership with People team
Technical Strategy & Roadmap
- Define and communicate clear engineering strategy and roadmap supporting business objectives (revenue, margins, new products, technical sustainability)
- Translate business objectives into concrete technical initiatives (new products, platform, productivity, keep-the-lights-on)
- Establish planning and review cycles (quarterly and annual planning, reviews, retrospectives) with Product and other functions
- Drive long-term investments in platform scalability, developer productivity, technical debt reduction, and infrastructure reliability
- Define and continuously improve engineering metrics (DORA, flow/cycle time, KTLO vs. new projects vs. improvements vs. productivity)
- Guide architecture decisions for backend services, AI systems, and browser-level infrastructure
- Own long-term evolution of technical architecture (backend, AI, browser technologies, cloud infrastructure)
- Prioritize structural investments (platform migrations, technical debt reduction, observability, developer productivity tools)
- Remain sufficiently hands-on to participate in code reviews, architecture reviews, and important technical decisions
- Own quality of products and services
Cross-Functional Collaboration
- Collaborate closely with Product, Data, and Sales teams to align technical execution with business priorities
- Manage technical request processes from different teams to ensure engineering resources are allocated to highest-impact initiatives
- Translate business objectives into clear technical strategies and engineering priorities
- Collaborate with CTO on overall technology direction and organizational planning
This role is ideal for a hands-on technical leader who enjoys staying close to code and architecture. While not coding daily, you will regularly participate in architecture discussions, code reviews, and technical decisions to ensure high technical standards while enabling the team to move quickly.
