Career Roadmap Series | Rajah Lehal – Founder and CEO,

Jessica Rowen

February 22, 2017

Everyone has a story to tell. Toronto hosts a vibrant tech ecosystem that continues to grow and make waves around the world. But the community is made up of individuals, each with their own experiences of triumph, struggle, detours and grit.

We’re launching this new Career Roadmap series to share just some of these many stories with you. Each post will put a spotlight on someone in the industry, what they’re doing and how they got there. We trust you’ll be encouraged in hearing their relatable experiences (including mistakes) and insights.

Introducing Rajah Lehal – Founder and CEO,

Rajah Lehal is the founder and CEO of, a legal tech company. When’s he’s not working (or thinking about work), he enjoys playing the board game “Power Grid” and watching financial thrillers – but not shows about entrepreneurship, these hit too close to home. In business school, he got Molson to agree to sponsor a Halo tournament he was organizing. He’s a big fan of UK reality TV star Lord Alan Sugar.

There were telltale signs that Rajah was destined for big things. That pressure is kind of on you when you skip multiple grades and graduate high school at 16 (as you do). A self-described computer nerd, and with encouragement from his father who worked in tech, Rajah entered the University of Waterloo to study math and computer science.

University was a formative time that saw two significant changes take place. Firstly, Rajah decided to shift his academic focus away from typically career-focused subjects to those in liberal arts he found genuinely interesting. At the same time, he began to attend and volunteer at entrepreneurial events outside of school to understand the startup scene and what it took to be an entrepreneur.

Rajah graduated from UWaterloo with an Honours degree in philosophy and a major course load in cognitive science, math and computer science. Afterwards, a co-op program led to a valuable opportunity with Bell Mobility. With almost no preparation or leadership experience, he found himself managing an IT team at the ripe old age of 19. Rajah faced various challenges but was able to navigate through them with the mentorship of his supervisors. His management experience left him with a growing taste for business and a consequent MBA from Ivey Business School at Western University, where he co-ran the student entrepreneurs organization.

He’ll tell you that it wasn’t part of his original plan but Rajah’s time at Western also included completing law school. Once again, his academic curiosity and inner tech nerd kicked in and he became fascinated by contracts which he saw as very similar to code in the compiling of language to work together.

Rajah’s career journey is a true culmination of his passions, experiences and brewing interest in entrepreneurship. After a decade of practising law at various firms, he started his own in 2009: Cobalt Lawyers focuses on tech law and is today comprised of eight staff.

Over time, Rajah identified a need for new lawyers to better understand how to drive contracts with its very technical language. And this wasn’t just an internal problem; clients had a similar issue of trying to make sense of contracts for the first time. There was a demand for something to enable easier onboarding to contract language, a customer-facing tool to get clients on the same page more quickly. And so, three years after his first business venture, Rajah founded Clausehound.

Today, Rajah enjoys the creative and multifaceted problem solving that comes with being CEO of a legal tech company. As someone who loves variety, he loves the excitingly unknown nature of what’s in the store for the week to come: business development, marketing, recruiting, product building. There are some exciting prospects on the horizon for Clausehound including social innovation projects on software and transparency which stem from Rajah’s advocacy for hacking justice.

But, of course, leadership isn’t without its struggles. Being an entrepreneur is a lot harder than Rajah anticipated. The last ten years have been a steep learning curve of getting from ideation to actualization. Working out pricing has been difficult. Recruitment and team training have been time-intensive.

Based on his experience, we asked Rajah what advice he had for for tech jobseekers and budding entrepreneurs. But really, these tips are valuable for anyone. Let’s keep them in mind as we continue to make Toronto’s tech ecosystem the best it can be.

  1. Be curious: Being open to different options can be how you find the type of job or business opportunity you’re looking.
  2. Volunteer: Get known as someone who people would want to work with. Opportunities will come when you go beyond what’s asked.
  3. Persevere: Entrepreneurship can be fatiguing both on time and money. Learn from your mistakes and keep at it. 

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