Building a legal function at a high-growth company means learning that templates from previous jobs only get you so far. “The process of building Jobber’s legal function required getting to know the business and designing a unique and customized roadmap based on how we do business here,” says Melissa Reiter, general counsel and senior director at Jobber, the Edmonton-based field service management platform. “And that roadmap is still changing.”
Reiter joined Jobber in January 2022 as the company’s first in-house lawyer. Since then, the company has grown from roughly 400 employees to approximately 1,200, with its platform now serving more than 100,000 businesses and 400,000 service professionals across 60 countries. Services invoiced through the platform have surpassed $100 billion – more than the GDP of some countries, Reiter notes. Her legal team has grown from one lawyer to four, a ratio held only by building lean, scalable systems from the ground up.
The road to four
The jump from 400 to 1,200 employees in four years put immediate pressure on legal to do more with far less margin for inefficiency. “It’s required us to be organized, have great systems, processes and be focused and clear in terms of the vision for the department,” Reiter says. She has been deliberate about team culture, treating mental health, collaboration, and well-being as equally important as performance. “That’s important to me as someone who’s building a team of people who are smart enough to do what they do anywhere,” she says. “And I’m glad that they choose to do it with me and with the folks at Jobber each day.”
The team stretches to keep pace with sharp internal colleagues, and AI literacy has become a particular focus – driven by the fact that Jobber’s broader workforce is already deeply technically fluent.
AI as an accelerator
Reiter is precise about how she frames AI’s role. It is not a replacement. “We’ve seen it as something that we are layering on top of processes. So instead we’re looking for opportunities whereby adding it into the mix, we can empower teams to change their workflows, to build it into their workflows, to make it an innovation partner and not just a replacement for something that exists, but an accelerator,” she says. “Our goal has been to use it to make space to focus on high-value and strategic work,” she adds. AI use in in-house legal departments has nearly doubled since 2024, with most teams planning to adopt it within the next two years, according to a Corporate Legal Operations Consortium report.
The clearest example of this shift for Jobber is NDA processing. One member of Reiter’s team took on a legal operations mandate and built an automated workflow using tools already available across the company, connecting systems to pull data from spreadsheets directly into template documents. NDA turnaround time dropped from 24 hours to roughly five to ten minutes. “That’s been a significant gain in terms of speed and flexibility, especially for a task that we get quite frequently,” Reiter says. The build required no outside vendor – just a lawyer willing to learn.
That experience shapes how Reiter now hires. She looks for candidates interested in legal operations as a specialization and treats comfort with AI tools as an advantage. “It would be an asset to any team to be able to say, this is how our business works – I can seamlessly navigate that, or I’m open to learning about it,” she says. The convergence of general counsel leadership and legal operations has emerged as a defining theme as AI reshapes practice.
Tracking a moving regulatory target
The legal risks Reiter monitors most closely shift with the direction of the business. AI regulation and privacy law rank among the highest priorities, with Canada's National Artificial Intelligence Strategy and its rapidly evolving federal privacy legislation just the latest examples. Fintech considerations also arise when Jobber processes customer invoicing and payments through third-party providers. “These areas move so quickly,” she says. The team uses AI to track regulations as they move through the legislative process – practising what they preach, as Reiter puts it. The subject matter is “quite liquid” at this stage, making close contact with internal business partners essential. She also collaborates with peers navigating similar cross-border regulatory complexity, both in Canada and abroad, to compare approaches in a regulatory landscape still taking shape. It reflects experience she developed in a previous role, navigating the complexities of the global travel industry during the pandemic.
External counsel play a distinct role where specialist depth is needed – in areas including fintech, advertising and marketing, AI, commercial leasing, labour and employment, and privacy. “Especially in specialized areas, we work with counsel who are living and breathing this, connecting with regulators, and can immediately say, I’m right on top of that issue, and I have a perspective on it,” Reiter says. “Those conversations are just tremendous in redirecting our thinking or adding value.”
Calm at the centre of the storm
The most underrated skill for any general counsel in a crisis is composure, says Reiter. “Being the calmest person in the room tends to be helpful, and I find that calm is contagious.” High-stakes situations trigger reactive instincts – the urge to respond quickly and get ahead of the problem – and the value a general counsel brings is the capacity to slow that down. “Slow is smooth and smooth is fast,” she says. “Trying to manage risk while in an escalated state is useful to no one.”
For lawyers considering a move to high-growth tech, adaptability, curiosity, and a willingness to let go of established processes are the qualities that count. “Focusing on practicality and efficiency and the execution of your risk management strategies is really key in this type of environment, and not getting too stuck on how you did things in the past, or how you are currently doing things,” Reiter says. At Jobber, a phrase she hears often captures it: what got us here won’t get us there.