Head of IT

Gorgias • Toronto, ON

5d • Hybrid

About The Position

We are seeking our first senior IT leader to define and operate the IT function at Gorgias. Currently, IT is partially outsourced and fragmented, which has been functional for our current size but will not scale with our growth trajectory towards $100M+ ARR, expanding global office presence, and increasing adoption of AI tooling. This role is part of the Finance department and reports to the CFO. The Head of IT will be responsible for IT infrastructure (both physical and software), SaaS software procurement, and global IT strategy. The position requires a blend of building and strategic thinking: as a builder, you will address fundamental issues like WiFi, tooling, access, and onboarding to ensure IT operations are seamless. As a strategist, you will design an operating model to support growth from $100M ARR to $500M and beyond without a proportional increase in IT headcount, integrating AI into IT operations. You will collaborate closely with Security Engineering, People, and Finance to establish infrastructure that provides Gorgias with the leverage of a Fortune 500 company while maintaining startup agility. This is a high-ownership role with significant scope, empowering you to shape the future of IT at Gorgias for the next five years.

Requirements

• 8–12 years in IT, including experience owning IT at a high-growth tech company.
• Track record building or transforming IT setups, not just maintaining them.
• Experience scaling IT operations >$100M.
• Deep experience in modern IT environments: SaaS-first, cloud-based, identity-driven (Okta, Google Workspace, Slack, etc).
• SOC 2 ownership end-to-end: scoping, evidence, audit coordination.
• Experience working alongside Security Engineering on access, devices, and compliance.
• Practical experience with AI tools and automation — comfortable building agentic workflows, not just consuming them.
• Vendor and procurement leadership, including managing AI tool spend at scale.
• Comfortable hands-on (will fix the WiFi) and at the strategy table (will own the roadmap).
• Thrive in ambiguity; comfortable building the path as you walk it.
• Act like an owner; bias for action comes from genuinely caring about the outcome.
• Operate with urgency; speed and quality are not mutually exclusive.
• Think at scale; build solutions and processes that hold up at 500+, not just at 240.
• Low ego; work in a highly collaborative fashion, effectively across teams with different priorities.
• Lead with integrity; hold yourself and others to a high bar, and match words with action.

Nice To Haves

• Knows how to find pragmatic, cost-effective solutions.

Responsibilities

• Define and own the multi-year IT roadmap, aligned to Gorgias' growth trajectory.
• Lead evaluation and rollout of AI-enabled IT tools; identify high-leverage use cases and build practical governance for responsible adoption.
• Architect AI-powered and agentic workflows that make onboarding, offboarding, and routine IT support nearly invisible.
• Translate business needs into scalable solutions, with clear tradeoffs at the table.
• Own the device lifecycle end-to-end: procurement, provisioning, refresh, recovery, secure disposal.
• Design self-service systems that scale with company growth without linear headcount growth.
• Manage identity and access across the SaaS stack, balancing security and usability.
• Own joiner / mover / leaver processes with least-privilege, role-based access, and periodic reviews.
• Lead a small IT support function and manage outsourced IT support team: set operating rhythms, runbooks, growth plans.
• Drive recurring-issue elimination through better tooling and automation — not just faster ticket closure.
• Track and improve service metrics: time to first response, time to resolution, CSAT, SLA adherence.
• Act as a sparring partner to teams selecting software tools — a center of excellence that helps identify, evaluate, and adopt the right solutions.
• Key partner in identifying AI tool strategy and spend (OpenAI, Anthropic, and the rest).
• Manage key software vendor relationships, renewals, and procurement workflows; centralize software knowledge and procurement database.
• Build vendor relationships that combine startup agility with enterprise-grade capabilities.
• Ensure every new hire has a consistent, secure, productive setup on day one.
• Oversee office technology reliability across global offices: WiFi, networking, conference rooms, AV.
• Maintain accurate inventory and lifecycle hygiene.
• Own and execute SOC 2 certification end-to-end, with efficient and automated evidence gathering.
• Partner with Security Engineering on endpoint controls, device compliance posture, and secure configurations.
• Support security incident response: triage, containment, device coordination, clear employee communications.
• Build playbooks for identity, email, and endpoint outages so failures are graceful, not chaotic.
• Own the IT budget; make thoughtful investment decisions within constraints.
• Lead key IT initiatives end-to-end with crisp stakeholder updates, predictable delivery, and measurable results.
• Partner with SRE and Engineering to create a cohesive infrastructure and tooling experience.
• Communicate the impact of operational improvements on company velocity.

Benefits

• 5-week vacation (We follow each country's appropriate PTO Laws)
• Paid sick leave
• Paid parental leave (16 weeks)
• MacBook Pro
• Private health insurance and retirement pension (RRSP with Gorgias matching up to 4%)
• For a smooth onboarding, we invite you to our Toronto office for one week (flights and accommodation handled by Gorgias)
• Get up to $900 CAD to set up your workstation at home
• Get up to $2,600 CAD of learning material per year (books, courses, training, and individual coaching)
• Every quarter, we organize a company-wide summit to discuss where we're going and strengthen social bonds. Once per year we organize offsite team retreats and company retreats!

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed