This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of IT based in Canada.
This is a strategic, hands-on leadership opportunity focused on transforming internal IT into a modern engineering and enablement function.
You will own the systems, business applications, automation, identity infrastructure, and internal AI tooling that support a globally distributed workforce.
The role combines long-term technology strategy with practical involvement in automation, integrations, security, and AI-enabled workflows.
You will lead IT Support and IT Tooling & Automation teams while setting a high technical and service standard across the organization.
A major focus will be accelerating AI adoption, improving productivity, and replacing repetitive manual processes with reliable automation and intelligent agents.
You will work closely with security, legal, AI enablement, and business stakeholders to balance innovation, governance, cost, and risk.
This role is ideal for a builder-leader who wants to shape how a modern technology company operates internally.
Accountabilities
- Own the internal IT strategy, roadmap, budget, vendor ecosystem, and overall technology operating model across support, business applications, integrations, automation, and AI tooling.
- Lead, develop, and mentor IT Support and IT Tooling & Automation teams, acting as an escalation point and setting technical and service standards.
- Manage IT as an internal product by defining service expectations, measuring employee experience, prioritizing high-impact initiatives, and communicating delivered improvements.
- Administer and continuously optimize business-critical SaaS platforms, including CRM, marketing, finance, HR, support, collaboration, and engineering tools.
- Design reliable API-driven integrations, data synchronization workflows, internal services, scripts, event-driven pipelines, CLI tools, and ChatOps solutions.
- Establish automated onboarding, offboarding, identity provisioning, and self-service capabilities to eliminate repetitive IT tasks.
- Own the internal AI tooling portfolio, including evaluation, procurement, administration, licensing, usage monitoring, cost governance, and lifecycle management.
- Introduce AI-powered assistants, knowledge retrieval, automated support workflows, ticket triage, and agentic automation into internal operations.
- Partner with AI enablement, security, and legal stakeholders to establish practical AI governance, data-handling standards, access controls, and responsible-use guardrails.
- Monitor AI adoption, usage, costs, and productivity gains to ensure technology investments deliver measurable business value.
- Oversee identity and device management, including SSO, SAML, SCIM, identity lifecycle automation, MDM, password management, and access reviews based on Zero Trust principles.
- Partner with security teams to maintain compliance and audit readiness, including ISO 27001 requirements, while embedding controls into automated processes.
- Drive root-cause analysis and continuous improvement across IT services, infrastructure, business applications, and employee-facing technology.
- Manage vendors, licensing, renewals, negotiations, consolidation initiatives, and the overall cost-versus-value of the technology portfolio.
- Establish a culture where recurring manual work is continuously identified and replaced with automation, self-service, or AI-assisted processes.
Requirements
- 10+ years of experience in IT engineering, business systems engineering, internal platform engineering, or a related discipline within SaaS or technology organizations.
- At least 3 years of experience leading teams responsible for internal business systems, automation, or technology platforms.
- Strong hands-on engineering background, including the ability to read, review, and contribute to automation code using Python or a comparable language.
- Strong understanding of APIs, webhooks, OAuth flows, integration frameworks, and cross-platform data synchronization.
- Proven experience owning and optimizing modern SaaS application environments, such as CRM, finance, HR, Google Workspace, Slack, Atlassian, GitHub, and Notion.
- Demonstrated experience deploying AI tooling within an organization, including LLM assistants, knowledge retrieval, AI-powered support, or agentic workflow automation.
- Practical understanding of AI administration, user access, seat management, usage governance, cost control, and responsible-use policies.
- Strong identity and security expertise covering SSO, SAML, SCIM, identity lifecycle automation, MDM, and Zero Trust access models.
- Experience supporting security and compliance requirements such as ISO 27001, SOC 2, or GDPR.
- Proven experience managing technology vendors, budgets, procurement, negotiations, licensing, and SaaS portfolio consolidation.
- Experience supporting globally distributed or remote-first teams with a strong focus on employee experience and service quality.
- Excellent written and verbal English communication skills, with the ability to work effectively with both technical and non-technical stakeholders, including executives.
- Strong leadership, strategic thinking, problem-solving, and prioritization skills, combined with a practical, hands-on mindset.
- Experience with agentic platforms, MCP, Claude, Gemini Enterprise, OpenAI, Copilot, or LLM-based internal agents is highly desirable.
- Familiarity with AI and cloud cost governance, usage analytics, per-seat economics, chargeback, or showback models is a plus.
- An SRE-oriented approach to internal IT, including SLIs/SLOs for employee-facing services, would be advantageous.
- Experience consolidating technology environments following periods of growth or M&A is also a strong plus.
Benefits
- 100% remote working, with the flexibility to work from the location where you are most productive.
- High-impact leadership position with significant visibility across the organization.
- Opportunity to shape internal IT strategy, automation, AI adoption, and technology infrastructure.
- Modern technology and AI environment with the freedom and resources to experiment and innovate.
- Culture that actively encourages automation and continuous improvement of internal processes.
- Opportunity to work with a self-motivated, multicultural, and progressive team.
- Strong autonomy and ownership over a strategically important area of the business.
How Jobgether works:
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best!
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
#LI-CL1
