Head of IT

TL;DR

Head of IT (SaaS/AI): Define and own multi-year IT roadmap and operations for high-growth SaaS company scaling to $500M+ ARR with an accent on AI-enabled tools, infrastructure, and global office support. Focus on architecting agentic workflows, automating onboarding/offboarding, achieving SOC 2 certification, and building scalable self-service systems.

Location: Toronto

Compensation: CA$172,250 – CA$190,381 + 0.009% – 0.019% equity

Company

Building a unified AI agent platform for conversational commerce in ecommerce, turning customer interactions into seamless relationships.

What you will do

• Define multi-year IT roadmap aligned to growth, evaluate and rollout AI-enabled tools with governance.
• Own device lifecycle, identity/access management, joiner/mover/leaver processes, and small IT support function.
• Manage SaaS procurement, vendor relationships, AI tool spend, and centralize software knowledge.
• Oversee endpoint fleet, office IT infrastructure (WiFi, AV, networking) across global offices.
• Execute SOC 2 certification, partner on security/compliance, support incident response.
• Own IT budget, lead initiatives, partner cross-functionally with Security, Engineering, People, Finance.

Requirements

• 8–12 years in IT, experience owning/transforming IT at high-growth tech >$100M scale.
• Deep expertise in SaaS-first, cloud-based, identity-driven environments (Okta, Google Workspace, Slack).
• SOC 2 ownership end-to-end, security collaboration, AI tools/automation hands-on.
• Vendor/procurement leadership, hands-on operations (e.g., WiFi fixes) and strategic roadmap.
• Thrive in ambiguity, owner mindset, scale thinking, low ego, collaborative.

Culture & Benefits

• 5 weeks vacation, paid sick/parental leave (16 weeks), private health insurance, RRSP matching up to 4%.
• MacBook Pro, $900 CAD workstation setup, $2,600 CAD annual learning budget.
• Quarterly company summits, annual offsites/retreats; premium AI tools access (#powerup channel, AI champions).
• One-week Toronto onboarding (flights/accommodation covered).