Job Description

Director of Software Engineering (Toronto Site Lead)
Location: Toronto, ON | Full-Time | Hybrid
We are looking for a Software Engineering Leader (Director or experienced Senior Manager) to build and scale our Toronto engineering office. This is a unique opportunity to help grow a cutting-edge AI-driven SaaS company.
In this role, you will grow the Toronto site into a high-performing engineering organization. You'll provide technical oversight, lead delivery, and establish a strong, collaborative culture. While focused on leadership, you'll remain close enough to the technology to mentor engineers and contribute to key technical decisions.
You will work directly with the VP of Software and collaborate with teams in California to ensure alignment on engineering direction, execution, and product vision.
Key Responsibilities
Build & Scale the Toronto Office
Hire and develop a team of 20-30 engineers (frontend, backend, ML/AI, data, devtools).
Create a strong, high-performance engineering culture.
Stay Technically Engaged
Maintain technical credibility and participate in architecture and design discussions.
Provide guidance on systems, design, and engineering best practices.
Develop & Mentor Talent
Recruit talent through strong relationships with Canadian universities and local markets.
Coach engineers, develop future leaders, and uphold engineering excellence.
Lead Delivery Across Value Streams
Own end-to-end product delivery from planning to adoption.
Partner with product, AI, and chip teams on roadmap execution.
Bridge Toronto & California
Ensure communication and alignment across distributed teams.
Establish effective engineering rituals and cross-site collaboration practices.
Ideal Experience
Leadership experience (Sr. Manager, Director) managing 15+ engineers.
10+ years in software engineering with progression from developer ? tech lead ? leader.
Technical depth in cloud-native systems, SaaS platforms, and AI/ML environments.
Strong track record delivering complex products and scaling engineering teams.
Skilled in hiring, mentoring, communication, and cross-site collaboration.
What We Offer
A pivotal opportunity to build and scale the Toronto engineering office.
Direct collaboration with senior and cross-disciplinary engineering leadership.
Strong connections to top Canadian universities and research institutes.
Competitive salary and early-stage equity.
A high-trust, low-ego culture focused on ownership, innovation, and collaboration.
Level & Growth Path
We are targeting Director-level candidates. However, strong Managers or Senior Managers who meet the criteria and are ready for the next step are encouraged to apply. The role can be scoped as Manager or Senior Manager with a performance-based promotion path as the site grows.
Technical Skills
Cloud-Native Architecture
SaaS Platforms
AI/ML Systems
Distributed Systems
Software Design & Architecture
DevTools & Developer Productivity
SDLC & Agile Execution
Delivery & Execution
Roadmap Ownership
End-to-End Product Delivery
Cross-Site Communication
Execution Planning
Risk Management
System Reliability & Best Practices
Soft Skills
Strategic Thinking
Communication
Culture Building
High-Performance Teaming
Stakeholder Alignment
Screening Questions
1. Leadership Experience
How many engineers have you directly managed at one time?
Have you scaled a team or site before? If yes, how large and in what timeframe?
2. Technical Background
Describe your experience with cloud-native systems (AWS, GCP, Azure, etc.).
What exposure do you have to AI/ML systems or data-intensive architectures?
3. Delivery & Execution
Provide an example of a product or feature you led from planning to launch.
How do you ensure delivery alignment across distributed or cross-functional teams?
4. Hiring & Talent Development
What role have you played in recruiting and onboarding engineers?
How do you coach engineers toward technical leadership?
Apply: sasha@talenttohire.com
Follow us at : https://www.linkedin.com/company/talenttohire

Skills Required