×
Register Here to Apply for Jobs or Post Jobs. X

Senior IT and Business Technology Lead

Job in Oakville, Ontario, B8B, Canada
Listing for: Property Law Firm CB LLP
Full Time position
Listed on 2026-03-10
Job specializations:
  • IT/Tech
    IT Support, IT Project Manager
Job Description & How to Apply Below
You’ve kept IT running. Now it’s time to own it.

You’ve maintained systems you didn’t design. Managed tickets you didn’t create. Proposed improvements that got shelved because “it’s not in the budget” or “not a priority.” You know what good IT looks like, and you’re watching it not happen where you are.

Maybe your current company treats IT like a cost center. Maybe you’re buried in a large team and only get to touch your corner. Or maybe you’re at a firm that hasn’t upgraded its tech stack in five years, and you’re starting to wonder if your skills are aging with it.

You don’t want to manage a team yet. You want to own something, end to end. Be the person who decides how IT works, not just executes someone else’s plan. That’s exactly what this role offers.

What this role is
Property Law is a national residential real estate law firm with 100+ employees across Ontario, Alberta, and BC. We don’t operate like a traditional law firm. We run on modern SaaS tools, think in systems, and treat technology as a competitive advantage, not overhead.

We’re hiring our first dedicated IT person, not a helpdesk technician, not a director. A senior individual contributor who will own IT and business technology across the company.

You’ll have an external IT partner for support and a COO who is deeply technical as your close collaborator. You won’t have a team on day one, but you will have full ownership over a function that affects how 100+ people do their work every day.

What you’ll do

Design IT end-to-end. Not just tools, but architecture: how systems connect, how people access them, and how data flows. We use Google Workspace, Slack, Dialpad, HiBob, Cloudflare, and a practice management system. You’ll own how it all fits together.

Run the vendor, don’t be run by them. Set expectations, evaluate their work, and step in when needed. You’re the single point of accountability.

Get hands-on. Configure, troubleshoot, integrate, whatever it takes. You know when to execute yourself and when to delegate.

Measure what matters. Define the metrics that show IT is working: onboarding speed, resolution times, uptime, security posture, tool adoption, cost efficiency.

Move the organization forward. Recommend tools, build training, run sessions, improve processes. You’re not just fixing problems, you’re helping the company get better at technology.

Work with data. Organize, query, and visualize business data with tools like Excel, Power BI, Snowflake, Grafana, or similar. Structured data and clear reporting are part of the job.

Who this role is for

You’ve owned IT end-to-end in a growing company or have been itching to and haven’t been given the chance.

You think in systems and architecture, not just tools and tickets.

You can manage a vendor relationship with authority.

You know exactly how to measure IT performance and have done it before.

You enjoy teaching people to use technology better, not just fixing their problems.

You’re comfortable with DNS, domain management, cloud platforms (AWS, Azure at a foundational level), and SaaS integrations.

You want to work somewhere technology decisions actually matter, and leadership gets it.

Who this role is NOT for

Someone looking to manage a team immediately.

Someone who thrives only in ticket-driven support.

Someone who experiments with tech without linking it to business outcomes.

Someone uncomfortable building from scratch, no processes, no IT metrics, no documentation yet.

Someone looking for a predictable, pre-built environment.

Why this role is worth your attention

You’ll own it all. Tools, architecture, metrics, outcomes. That level of ownership in a company this size is rare.

We’re scaling. Property Law is actively growing, acquiring, and innovating. Your decisions will have a direct impact on hundreds of real estate transactions across multiple provinces.

Leadership understands technology. Our COO is deeply technical. You won’t waste time explaining basics or fighting for budget.

You’ll help push an entire industry forward. Legal tech is behind the times and we’re changing that.

You won’t be alone. Vendor support and an engaged, technical COO are on your side.

The practical stuff

Location:

GTA preferred…
Position Requirements
10+ Years work experience
Note that applications are not being accepted from your jurisdiction for this job currently via this jobsite. Candidate preferences are the decision of the Employer or Recruiting Agent, and are controlled by them alone.
To Search, View & Apply for jobs on this site that accept applications from your location or country, tap here to make a Search:
 
 
 
Search for further Jobs Here:
(Try combinations for better Results! Or enter less keywords for broader Results)
Location
Increase/decrease your Search Radius (miles)

Job Posting Language
Employment Category
Education (minimum level)
Filters
Education Level
Experience Level (years)
Posted in last:
Salary