Director, IT & Operations

Jobber•Toronto, ON

2d•CA$181,400 - CA$245,400•Hybrid

About The Position

Jobber is seeking a strategic IT leader to join their IT & Security department as the Director, IT and Operations. This role is crucial for driving operational excellence, security, and scalability within the company. Jobber focuses on empowering small home service businesses with technology to manage quoting, scheduling, invoicing, and payments, enhancing customer experience. The company has a strong culture recognized by various accolades and is committed to employee professional growth through extensive onboarding resources, mentorship opportunities, and supportive leadership focused on work-life harmony. The IT & Security team's mission is to ensure Jobber's people, data, and infrastructure are secure, reliable, and scalable. The Director, IT and Operations will lead the IT function, encompassing IT Engineering and IT Operations, serving as the technological backbone for all employees. This includes responsibility for end-user support, networking, infrastructure, hardware lifecycle management, shared software and AI tooling, and the physical IT presence across Jobber's offices.

Requirements

Progressive IT experience, including demonstrated leadership of multi-level teams spanning both IT engineering and IT operations functions.
A track record of scaling a team’s output with AI and automation, reaching for leverage before headcount.
Proven ability to develop and execute IT strategies aligned to business goals, with a track record of planning ahead of scale.
Hands-on experience with Apple hardware, Google Workspace, cloud-based MDMs, and next-gen endpoint security products such as CrowdStrike and JAMF Protect.
Deep knowledge of networking, systems architecture, identity and access management (Okta), and security best practices.
Experience managing IT budgets, vendor relationships, and contract negotiations.
Strong understanding of compliance and security regulations relevant to a scaling technology company.
Demonstrated ability to lead cross-functional projects from inception through delivery.
A player/coach mindset: you can set strategic direction and roll up your sleeves when needed.
Experience leading the IT scope of office moves, openings, or expansions across multiple locations.

Nice To Haves

Experience at a growing SaaS or technology company at a similar stage to where Jobber is heading, with insight into how to build ahead of growth.
Direct experience supporting an organization through audits or significant compliance scale-up events.

Responsibilities

Define and execute a forward-looking IT strategy that aligns with Jobber’s business goals and growth trajectory, building ahead of our growth, not reacting to it.
Champion best practices in security, compliance, and operational scalability across the organization.
Build, mentor, and manage an organization of approximately 15 people across two teams: IT Engineering, focused on systems and infrastructure, and IT Operations, focused on end-user support and hardware logistics, with direct reports at the manager or senior individual contributor level and a broader team beneath them.
Ensure the IT help desk delivers an exceptional internal support experience with timely, high-quality resolution, and develop training programs and career pathways that cultivate technical skills and retain top talent.
Operate as a player/coach: set strategic direction and have the experience and knowledge to go deep when needed, leading through your team rather than around them.
Own the physical IT footprint of our offices: networking, meeting-room and AV technology, on-site hardware, and the in-office employee experience, including leading the IT scope of office moves, openings, and expansions from day one.
Partner with Workplace/People Experience, Security, and vendors to deliver office projects on time and on budget across regions.
Oversee networking and infrastructure; including Meraki and UI hardware, ensuring security, scalability, and reliability, while leading identity and access management strategy toward a zero-trust architecture.
Own disaster recovery and business continuity planning for shared IT services and hardware.
Manage end-to-end hardware procurement, deployment, and lifecycle management across multiple regions, building scalable inventory and logistics processes to ensure timely, cost-effective distribution of IT assets, and overseeing device decommissioning and hardware refresh programs.
Own shared software and AI tooling including Okta, Claude, Google Workspace, Zoom, Slack, and Atlassian; managing licensing, vendor relationships, and usage scaling while partnering with departments to meet software needs cost-effectively.
Ensure employee identity and access management processes are streamlined for both compliance and efficiency.
Use AI and automation as a force multiplier to scale IT’s capacity and service quality and give the whole company access to leading-edge AI tools, owning the platforms, licensing, and responsible-use guardrails behind them in partnership with Security.
Collaborate closely with the Security team on cybersecurity and data privacy across IT systems, implementing and enforcing Jobber’s security policies, and preparing and supporting the organization through audits and significant compliance milestones.
Represent the IT function with senior leadership, driving visibility into roadmap, risks, and resource needs across the organization.