Head of Engineering

Stay22 • Montreal, QC

46d • Onsite

About The Position

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.
Reporting directly to the CTO, the Head of Engineering will oversee a growing engineering organization of ~40 engineers across several squads, managing a small group of Engineering Managers and senior technical leaders. You will partner closely with Product, Data, and Commercial leadership to translate ambitious product goals into scalable technical systems and high-impact engineering roadmaps.
This role is ideal for a hands-on technical leader who still enjoys being close to the code and architecture. While you won’t be coding day-to-day, you will regularly participate in architecture discussions, code reviews, and technical decision-making, ensuring the team maintains high technical standards while moving quickly.
You will own the engineering roadmap and technical strategy, working across squads to balance new product development with platform health, scalability, and long-term technical investments. As a leader of leaders, you will focus on building strong engineering management practices, developing senior talent, and fostering a culture of innovation, ownership, and operational excellence.

Requirements

• English proficiency required for daily communication with international colleagues and team members
• 15+ years of experience in software engineering, with significant experience building scalable systems and platforms
• 5+ years of experience in engineering leadership, including managing managers and leading multi-team engineering organizations
• Proven experience operating in startup or scale-up environments, where speed, ownership, and adaptability are essential. Experience scaling from ~30 to 100+ engineers is a strong plus
• Track record as Head of Engineering / VP Engineering in a B2B SaaS, marketplace, or ad/affiliate‑driven 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 (e.g., GPT, Claude) and their practical applications in production environments
• 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
• Demonstrated ability to re‑prioritize engineering portfolios (new product vs platform vs productivity) in response to business shifts, and to align stakeholders around those choices.
• Excellent communication and stakeholder management skills; comfortable working closely with executive leadership, board‑level stakeholders, and cross‑functional peers.

Responsibilities

• Lead and scale a high-performing engineering organization of ~40 engineers across multiple squads, with clear expectations on quality, ownership, collaboration, and speed
• Evolve the engineering org structure (squads, platform vs product, EM layer, TLs, Staff/Principal roles) as the company scales
• Own the engineering hiring bar and process, especially for senior talent (Staff/Principal, EMs, Heads).
• Implement robust performance, feedback, and growth processes that are fair, transparent, and aligned with company values.
• Address misalignment or under‑performance at all levels with clarity and empathy.
• Build strong engineering management practices, including performance calibration processes, career development frameworks, and leadership mentorship
• Foster a culture of ownership, technical excellence, and continuous improvement across the engineering organization
• Build a strong succession pipeline for critical roles (Tech Leads, EMs, Staff Engineers).
• Establish clear career ladders and leveling for ICs and managers, and partner with People team on promotions and compensation frameworks.
• Define and communicate a clear engineering strategy and roadmap that supports company‑level outcomes (revenue, margins, product bets, and tech sustainability).
• Translate business goals in Travel, Retail, and Out-Of-Open-Web into concrete technical portfolios (new product, platform, productivity, and KTLO).
• Create and maintain the right planning and review cadences (quarterly/annual planning, reviews, retros) with Product and other functions.
• Drive long-term investments in platform scalability, developer productivity, technical debt reduction, and infrastructure reliability
• Select and continuously refine engineering metrics (e.g., DORA, flow/cycle time, KTLO vs new vs improvement vs productivity), and ensure they inform decisions not vanity dashboards
• Guide architecture decisions across backend services, AI systems, and browser-level infrastructure
• Own the long‑term evolution of our technical architecture across backend services, AI systems, browser technology, and cloud infrastructure (GCP‑like).
• Sponsor and prioritize foundational investments (platform migrations, tech‑debt programs, observability, developer productivity tooling).
• Remain hands-on enough to participate in code reviews, architecture reviews, and key technical decisions
• Be accountable for the quality of our products and services
• Partner closely with Product, Data, and Commercial leadership to align engineering execution with company priorities
• Lead technical intake processes across departments to ensure engineering resources are focused on the highest-impact initiatives
• Translate business goals into clear technical strategies and engineering priorities
• Collaborate with the CTO on overall technology direction and organizational planning
• Work with Security/Legal on security programs, privacy, and compliance (e.g., SOC2‑like expectations, GDPR/PIPEDA, DPAs, fingerprinting/data‑sharing constraints).
• Oversee the health and scalability of Stay22’s core platform, including backend services, data pipelines (in partnership with head of data), our hub
• Guide best practices around testing, observability, monitoring, and operational resilience
• Ensure the engineering organization maintains high standards for security, privacy, and system reliability, including implementing recommendations from future security leadership
• Champion engineering tooling, development workflows, and operational improvements that increase team productivity and platform quality
• Drive cross-squad initiatives that improve the effectiveness and cohesion of the engineering organization
• Align technical strategy with the company’s growth plans and product vision
• Act as a key technical voice within the leadership team, contributing to broader company strategy and decision-making

Benefits

• Support Travel Creators: Be part of a team that empowers travel creators to explore the world by increasing their passive income potential.
• Empower Your Growth: We hire champions and give them the opportunity to excel, skipping levels and honing their superpowers.
• Lead with Impact: We empower our team members to take charge and make a real impact in the Stay22 universe.
• Location, Location, Location: Enjoy our bright and vibrant office in the heart of Little Italy, surrounded by great shops and restaurants
• Be Yourself: Embrace a come-as-you-are dress code and a flexible work schedule.
• Comprehensive Benefits: We offer health & dental benefits, retirement plans, learning & development opportunities, and social & team-building activities, including exciting retreats.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees