Head of IT at Gorgias in Toronto, Ontario, Canada

We believe conversations will become the #1 way to shop. At Gorgias, we’re building the platform that makes this real: a unified AI agent that sells, supports, and re-engages customers across the entire journey. Conversational Commerce is the future of ecommerce, and we’re leading that shift. Our mission is to turn every interaction between a brand and its customers into a relationship: personal, seamless, and intelligent. By combining deep product expertise with the latest in AI, we’re making shopping feel more natural, human, and connected than ever before. To win, we focus relentlessly on: - Quality: conversations that feel authentic and on-brand. - Experience: effortless shopping from chat to checkout. - Re-engagement: personal, 1-1 dialogue instead of noisy marketing. The opportunity is massive. As AI reshapes how people buy, Gorgias is building the foundation for the next decade of ecommerce, where every brand has its own intelligent agent and every customer feels understood. Join us to make Conversational Commerce real. ABOUT THE ROLE We're hiring our first senior IT leader to define how IT operates at Gorgias. Today, IT is partially outsourced and fragmented. That's worked at our current size, but it won't scale with our path to $100M+ ARR, a growing global office footprint, and the volume of AI tooling we're adopting every quarter. This role sits within Finance and reports to the CFO. You'll own IT infrastructure (physical and software), SaaS software procurement and IT strategy globally. The job is half builder, half strategist. As builder, you'll fix the basics — WiFi, tooling, access, onboarding — and make day-to-day IT feel invisible. As strategist, you'll design the operating model that takes us from 100M ARR to 500M and beyond without linear IT headcount growth, and put AI at the core of how IT runs. You'll partner closely with Security Engineering, People, and Finance to build infrastructure that gives Gorgias the leverage of a Fortune 500 — and the speed of a startup. This is a high-ownership role with real scope: you will define what IT looks like at Gorgias for the next five years. MISSION Build a reliable, scalable, AI-first IT function that lets Gorgias grow from 100M ARR to 500M+ ARR — and makes infrastructure, tooling, and access feel invisible to the rest of the company. WHAT YOU'LL DO 🤖 IT STRATEGY & AI ENABLEMENT - 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 ⚙️ IT OPERATIONS & SERVICE DELIVERY - 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 💸 PROCUREMENT & VENDOR MANAGEMENT - 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 💻 ENDPOINT FLEET, OFFICE IT & WORKPLACE INFRASTRUCTURE - 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 - Knows how to find pragmatic, cost-effective solutions 🔒 SECURITY, COMPLIANCE & RESILIENCE - 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 📈 BUDGET, DELIVERY & CROSS-FUNCTIONAL LEADERSHIP - 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 HOW WE MEASURE SUCCESS - AI is doing the work. Agentic workflows handle the majority of onboarding, offboarding, and routine IT support - The basics are quietly excellent. WiFi, networking, AV, and day-one setup all work, every time, in every office - Stack is governed. SaaS and AI tooling are centralized, cost-managed, and consolidated where it makes sense - SOC 2 is delivered. Certification achieved on schedule with audit-ready, automated evidence - IT is proactive, not reactive. Recurring issues are eliminated, not just resolved - Service metrics trend right. TTFR, TTR, CSAT, and SLA adherence all measured and improving - IT is a strategic partner. Trusted by Security, Engineering, People, and Finance — not a function called only when things break WHAT WE'RE LOOKING FOR EXPERIENCE - 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) HOW YOU OPERATE - You thrive in ambiguity. You're comfortable building the path as you walk it. - You act like an owner. Your bias for action comes from genuinely caring about the outcome, not from performing urgency. - You operate with urgency. Speed and quality are not mutually exclusive. - You think at scale. You build solutions and processes that hold up at 500+, not just at 240. - You are low ego. You work in a highly collaborative fashion, effectively across teams with different priorities. - You lead with integrity. You hold yourself and others to a high bar, and you match your words with action. This is a builder role. You will define what IT looks like at Gorgias for the next five years. PERKS & 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! AI at Gorgias At Gorgias, AI is a natural extension of how we work and build. Our teams use it every day to research, write, analyze, code, and craft better customer experiences. Everyone has access to premium AI tools (ChatGPT, Claude, Granola & others) and an annual L&D budget to explore new ones. The real magic happens when we share what we learn. Our #powerup Slack channel is a digital petri dish of new tools and workflows, and each team has AI champions who showcase fresh ideas during weekly company-wide standups, now practically AI demo sessions. We see AI not as a replacement for creativity or empathy, but as a multiplier, helping us move faster, think deeper, and serve customers better. AI use in Recruiting at Gorgias By submitting your application, you agree that Gorgias may collect and process your personal data for recruiting, workforce planning, and related purposes. For more information about how we process your data and your rights, please refer to our Applicant Privacy Policy https://www.gorgias.com/legal/applicant-privacy-policy. Diversity & Inclusion at Gorgias We’re committed to creating an inclusive environment where everyone can thrive. We welcome applicants from all backgrounds, experiences, and perspectives because diverse teams drive innovation and better decision-making. If you need accommodations during the application or interview process, please contact us at accommodation@gorgias.com.