Director of Software Engineering; SAAS​/AI​/ML

Position: Director of Software Engineering (SAAS/ AI/ ML)

Director of Software Engineering (AI/ ML / SAAS - Startup)

Location: Downtown Toronto, Full-Time | Hybrid 4 days

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.

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.

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
• SDLC & Agile Execution

Delivery & Execution

• Roadmap Ownership
• End-to-End Product Delivery
• Cross-Site Communication
• Execution Planning
• System Reliability & Best Practices

Soft Skills

• Strategic Thinking
• Communication
• Culture Building
• High-Performance Teaming
• Stakeholder Alignment

Screening Questions

• 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?
• Describe your experience with cloud-native systems (AWS, GCP, Azure, etc.).
• What exposure do you have to AI/ML systems or data-intensive architectures?
• 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?
• What role have you played in recruiting and onboarding engineers?
• How do you coach engineers toward technical leadership?

Apply

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