Director of Engineering

Director of Engineering

Hybrid (Toronto)

Are you a hands-on engineering leader who thrives at the intersection of technology, strategy, and people leadership?

We're seeking a Director of Engineering to lead globally distributed engineering teams responsible for building and scaling high-volume, cloud-native applications. This is an exceptional opportunity for a technical leader who enjoys solving complex architectural challenges, mentoring engineers, and partnering with business stakeholders to drive innovation and product delivery.

What You'll Do

As Director of Engineering, you'll lead a team of talented engineers across North America and India while shaping the technical direction of our products and platforms.

Leadership & Team Development

• Lead, mentor, and grow a team of 20-30+ software engineers across multiple regions and time zones.
• Foster a collaborative, high-performance engineering culture focused on ownership, accountability, and continuous improvement.
• Coach and develop senior engineers and engineering managers while building a strong talent pipeline.

Technical Leadership

• Own architecture and system design decisions across the technology stack.
• Drive the evolution of large-scale distributed systems running on AWS.
• Provide technical guidance and stay close enough to the codebase to challenge assumptions, mentor engineers, and make sound architectural decisions.
• Lead modernization initiatives, including cloud-native transformations and legacy application modernization.

Cross-Functional Collaboration

• Partner closely with Product, Business, and Executive stakeholders to align engineering initiatives with strategic objectives.
• Translate business priorities into scalable technical roadmaps.
• Influence organizational technology strategy and engineering best practices.

Delivery & Execution

• Own successful delivery of product and platform roadmaps.
• Improve engineering efficiency through modern development practices, tooling, automation, and Agile delivery methods.
• Remove organizational impediments and enable teams to execute effectively.

Engineering Excellence

• Champion software craftsmanship, testing strategies, code quality, and operational excellence.
• Enhance observability, monitoring, incident management, and system reliability.
• Drive adoption of AI-powered development tools and workflows that improve engineering productivity and quality.

Required Qualifications

• 7+ years of software development experience.
• 3+ years of engineering leadership experience managing teams of 20+ professionals.
• Proven experience hiring, mentoring, developing, and managing high-performing engineering teams.
• Strong technical background in: Java, Angular, React, or Vue.js, API design and distributed systems

Preferred Qualifications

• Experience modernizing large-scale legacy Java applications.
• Experience supporting multi-region AWS deployments.
• Experience leading platform modernization and digital transformation initiatives.
• Prior experience in fast-growing SaaS, travel technology, hospitality technology, fintech, or enterprise software environments.

Technical Expertise

You should possess deep expertise in: Monolithic and Microservices architectures, Event-Driven Architecture, Cloud-native application development, Scalability, resiliency, and reliability engineering, Modern API design patterns, System design trade-offs and architectural decision-making

Database Technologies

Experience working with: Oracle, PostgreSQL, Other relational database technologies. Including: Data modeling and schema design, Query optimization, Performance tuning

As well as NoSQL technologies such as: DynamoDB, MongoDB, Cassandra, and understanding when to leverage each platform effectively.

AWS Cloud Expertise

Strong production experience with AWS services, including: EC2, ECS / EKS, Lambda, VPC, RDS, DynamoDB, CloudFormation, Terraform

You should have a track record designing, deploying, and operating cloud-native systems at scale.

AI-Driven Software Development

We are looking for a leader who actively leverages AI throughout the software development lifecycle, including:

• Coding assistants
• AI-powered code reviews
• Test generation
• Agentic workflows
• Developer productivity platforms

You should be able to demonstrate measurable ways AI has improved velocity, quality, and engineering outcomes within your teams.

Education

• Bachelor's degree in Computer Science, Engineering, or a related technical discipline.

Why This Opportunity?

This role is ideal for a leader who wants to remain technically credible while influencing engineering strategy, architecture, culture, and organizational growth. You'll have the opportunity to lead distributed teams, solve complex technical challenges, and help shape the future of a rapidly evolving technology organization.