Head of Engineering (TubeBuddy)

GameSquare Holdings Inc. is a cutting-edge media, entertainment, and technology company, and they are seeking a Head of Engineering for TubeBuddy. The role involves owning the engineering strategy, execution, and team health while partnering with various departments to enhance product quality and reliability using AI-enhanced engineering tools.

Responsibilities:

• Lead and mentor the engineering team; grow talent and set expectations
• Own engineering hiring, onboarding, and team health
• Foster a healthy, high-performance culture with clear standards and feedback
• Set technical strategy across our web stack and architecture
• Refine and improve standards for quality, reliability, and performance across products
• Ensure we ship user-facing web products at a strong pace without compromising quality
• Partners closely with Business Development/Product, Operations, Design, Marketing, and Customer Support to deliver creator-focused value
• Guide cross-functional adoption of AI tools and identify synergy opportunities
• Develop and influence operational processes and culture across the functional org

Requirements:

• Proven engineering leader who has owned outcomes for product-driven teams, including roadmap execution, team health, and delivery predictability
• Strong technical judgment across legacy and modern web stacks, and system architecture, with a track record of making durable tradeoffs on reliability, performance, security, and maintainability
• Practiced in iterative discovery and delivery, using lightweight experiments and fast feedback loops to confirm direction, quantify impact, and avoid overbuilding
• Experience with AI coding tool adoption at the engineering team or org level, with demonstrated ability to set organizational standards and drive effective implementation
• Demonstrated ability to use AI-assisted tooling efficiently and reliably, including setting norms for responsible use, establishing validation processes, and protecting sensitive data throughout the development workflow
• Comfort operating in a small team with hands-on influence, balancing strategic leadership with tactical execution and contributing directly to technical decisions and implementation
• Clear, collaborative communication across technical and non-technical stakeholders, with ability to translate complex technical concepts into actionable insights for cross-functional partners
• Experience with .NET/C# (soft requirement)
• Experience with data engineering platforms
• Familiarity with YouTube or the creator economy
• Experience scaling processes in lean teams