Head of AI Engineering & System Architecture

Siena AI; Toronto; On-site; CAD 120,000 - 160,000; Full time

Job summary

A forward-thinking AI company in Toronto is seeking a Head of Engineering to lead the technical vision for an innovative customer experience platform. The ideal candidate will have a successful track record of scaling teams, a deep knowledge of AI technologies, and the ability to collaborate with leadership. This role offers a significant impact on product development and the opportunity to work in a dynamic and inclusive environment.

Benefits

Competitive salary

Opportunity for equity or stock grants

Learning budget

Qualifications

• Scaled teams to 30+ successfully.
• Proficient in using AI tools.
• Technical depth in AI-native fluency.
• Comfortable with customer engagement.
• High agency and proactive shaping abilities.
• Led teams that regularly shipped at scale.
• Made impactful technical decisions.
• Developed leaders from individual contributors.
• Maintained velocity during growth periods.
• Experienced with conversational AI and API integrations.
• Ability to switch between strategy and debugging.
• Possess startup DNA and comfort with ambiguity.

Responsibilities

• Set technical roadmap aligned to business goals.
• Double the engineering team over 12-18 months.
• Stay hands-on with AI tools and write prototypes.
• Operate cross-functionally with peers.
• Drive velocity at scale and manage team dynamics.
• Build a strong culture to attract top talent.

Skills

Team scaling

Hands-on AI coding

Technical depth in AI

Customer relations

Proactive direction shaping

Leadership development

High growth velocity maintenance

Experience with relevant technology

Fluid from strategy to debugging

Positive culture building

Startup adaptability

Tools

Cursor

Claude Code

Codex

Job description

A forward-thinking AI company in Toronto is seeking a Head of Engineering to lead the technical vision for an innovative customer experience platform. The ideal candidate will have a successful track record of scaling teams, a deep knowledge of AI technologies, and the ability to collaborate with leadership. This role offers a significant impact on product development and the opportunity to work in a dynamic and inclusive environment.