Head of Engineering

Posted 3 days ago

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About the role

  • Head of Engineering overseeing ~40 engineers at Stay22, advancing technical vision and strategy in a hybrid role.

Responsibilities

  • Lead and grow a high-performing engineering organization of about 40 engineers organized into multiple squads, with clear expectations around quality, ownership, collaboration, and speed of delivery
  • Evolve the engineering organization structure (squads, platform vs. product, Engineering Managers layer, Tech Leads, Staff/Principal roles) as the company scales
  • Own engineering hiring standards, with a particular focus on senior hires
  • Establish robust performance, feedback, and career-development processes that are fair, transparent, and aligned with company values
  • Manage misalignment or underperformance at all levels with clarity and empathy
  • Develop strong engineering management practices, including performance calibration, career-development frameworks, and mentoring for leaders
  • Foster a culture of ownership, technical excellence, and continuous improvement
  • Build strong succession and backfill plans for critical roles (Tech Leads, Engineering Managers, Staff Engineers)
  • Define career ladders and clear levels for ICs and managers, partnering with the People team for promotions and compensation structures
  • Define and communicate a clear engineering strategy and roadmap that supports company goals (revenue, margins, new products, technical sustainability)
  • Translate business objectives into concrete portfolios of technical initiatives (new products, platform, developer productivity, KTLO)
  • Put in place appropriate 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

Requirements

  • Fluent English required for daily communication with international colleagues and teams
  • 15+ years of software engineering experience, including designing scalable systems and platforms
  • 5+ years of engineering leadership experience, including managing managers and multi-team organizations
  • Demonstrated experience in a startup or scale-up environment, where speed, ownership, and adaptability are critical
  • Experience as Head of Engineering or VP Engineering in a B2B SaaS, marketplace, or advertising/affiliation environment
  • Strong modern backend technical experience (JavaScript/TypeScript, Node.js, Python)
  • Experience with cloud platforms (GCP preferred) and scalable distributed architectures
  • Solid knowledge of AI/ML systems and modern LLM tools (e.g., GPT, Claude) in production environments
  • Proven ability to review architectures, guide technical decisions, and retain credibility with senior engineers
  • Experience with engineering performance metrics (e.g., DORA metrics) and improving engineering operations
  • Strong cross-functional leadership and collaboration skills with Product, Data, and business teams
  • Excellent communication and stakeholder-management skills, including engagement with executive leadership and the board

Benefits

  • Health insurance, dental coverage, retirement plan, training, and team activities

Job type

Full Time

Experience level

Lead

Salary

Not specified

Degree requirement

Bachelor's Degree

Tech skills

CloudGoogle Cloud PlatformJavaScriptNode.jsPythonTypeScript

Location requirements

HybridMontrealCanada

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