Director, IT & Operations (Toronto)

Are you a strategic IT leader who thrives at the intersection of operational excellence, security, and scalability? Then Jobber might be the place for you! We’re looking for a Director, IT and Operations to be part of our IT & Security department.

Jobber exists to help people in small businesses be successful. We work with small home service businesses, like local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber they can quote, schedule, invoice, and collect payments from their customers, while providing an easy and professional customer experience. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want!

The Team

The IT & Security team’s mission is to keep Jobber’s people, data, and infrastructure secure, reliable, and scalable as the company grows. As Director, IT and Operations, you will lead the IT function, spanning IT Engineering and IT Operations, serving as the internal technology backbone that every Jobberino relies on to do their best work. Your teams are responsible for the end‑user support experience, networking and infrastructure, hardware lifecycle, shared software and AI tooling, and the physical IT footprint across Jobber’s office locations.

The Role

As Director, IT and Operations, you will own and execute Jobber’s IT strategy across IT Engineering and IT Operations to support our high‑growth business. Reporting to the Senior Director, IT & Security, you will lead an organization of approximately 15 people, including people managers and individual contributors, across multiple offices. You will pair strategic ownership with a hands‑on leadership style to oversee networking and infrastructure, hardware procurement and logistics, shared software and AI tooling, and the physical IT footprint of our offices, keeping everything scalable, secure, and operationally excellent.

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.

Qualifications

• 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.

Preferred Qualifications

• 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.

Location

This role is based out of Jobber’s Toronto office. You will be expected to work on‑site a minimum of three days per week, with quarterly travel to Jobber’s other office locations as needed.

Compensation

Minimum annual salary of $181,400CAD, a midpoint of $213,500CAD, and a maximum salary of $245,400CAD, designed to reflect the progression from learning the ropes to truly excelling. Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

Benefits

• A total compensation package that includes an extended health advantages package with fully paid premiums for both body and mind, matching in RRSP, TFSA or FHSA, and stock options.
• A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.
• Opportunity to build, grow, and leave your impact on a $400‑billion industry that has no dominant player…yet.
• To work with a group of people who are humble, supportive, and give a sh*t about our customers.

We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.