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The Leadership Agency

Director of Cloud Engineering

Posted 17 Days Ago
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In-Office
Toronto, ON, CAN
Senior level
In-Office
Toronto, ON, CAN
Senior level
The Director of Cloud Engineering will lead a multi-year cloud transformation, build and mentor a cloud engineering team, manage infrastructure, and collaborate with various teams to optimize performance and security.
The summary above was generated by AI


Our client is a fast-growing, purpose-driven organization on a mission to redefine the customer experience in the service industry. With their people-first approach, they’re scaling rapidly and transforming how everyday services are delivered — all while building a world-class workplace culture. 

Led by a visionary founder and a high-performing executive team, the company has experienced consistent double-digit growth and is on track to be a $1B company. They’ve built a reputation for operational excellence, innovation, and cultivating award-winning teams across North America.

We’re looking for a strategic and hands-on Director of Cloud Engineering to lead a transformative cloud journey and architect the foundation of a modern, scalable tech ecosystem. This is a high-impact leadership role ideal for someone who’s passionate about innovation, experienced in large-scale digital transformation, and excited to build the infrastructure that supports rapid product delivery across multiple business lines.

Cloud Strategy & Modernization:
  • Own and lead the multi-year cloud transformation strategy — evolving legacy systems into scalable, secure, cloud-native platforms
  • Enable product-led growth by building infrastructure that supports a portfolio of customer-focused services
  • Drive standardization and scalability across multiple brands and business units
Team Leadership & Growth:
  • Build, grow, and mentor a high-performing cloud engineering team
  • Foster a culture of ownership, technical excellence, and continuous improvement
Infrastructure & Operations:
  • Oversee cloud architecture, deployment, performance, and disaster recovery strategies
  • Ensure reliability, severability, and high availability across environments
Collaboration & Enablement:
  • Work closely with Engineering, Product, Security, and Data teams to deliver reliable, self-serve infrastructure
  • Enable agile product teams with the tools and automation needed for fast, secure delivery
Innovation & Optimization:
  • Champion modern DevOps practices, infrastructure-as-code, and CI/CD pipeline
  • Continuously seek out opportunities to improve scalability, reduce costs, and streamline operations
Cost & Vendor Management:
  • Manage cloud spend across business units and drive ROI through smart investment and vendor partnerships
  • Lead negotiations and maintain strong relationships with cloud service providers
Security & Compliance:
  • Ensure infrastructure meets high standards for security, data governance, and compliance
  • Collaborate with Security teams to implement and enforce controls and best practices


Requirements
  • Cloud Architecture Expertise: Deep experience designing and operating cloud environments (AWS, Azure, or GCP) supporting high-traffic, customer-facing platform
  • Transformation Experience: Proven success driving cloud migrations or infrastructure modernization at scale
  • Product-First Thinking: You understand how infrastructure empowers product and how to deliver speed without compromising security or performance
  • Leadership DNA: A track record of hiring, growing, and retaining top engineering talent
  • DevOps Savvy: Familiarity with infrastructure-as-code tools (like Terraform), containerization, CI/CD workflows, and severability platforms
  • Strategic Communication: You think long-term, communicate clearly, and build trust across technical and non-technical teams
  • Bonus Points: Experience supporting multiple brands or shared platforms across a distributed environment


Benefits
  • Join a team that’s a recognized leader in its industry
  • Competitive compensation package with great benefits
  • Focus on personal and professional growth
  • A mission-driven, high-energy workplace that puts people first



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