Canadian Legal Technology: CEO Law

Last month, I had the pleasure of chatting with Steve Monk, who is the CEO of both CEO Law and CEO Law Technology, both founded in 2017 and based in Toronto, Canada. The tag line for CEO Law is as follows: 

Senior, Bay Street Lawyers available to Your Company at $200 to $250/hr. CEO Law®– committed to happy Customers, Employees and Owners, in that order!

For those not familiar with Canadian geography, Bay Street is the equivalent of Wall Street and the quoted rate is a deal. 

Mary Juetten: What problem are you solving?

Steve Monk: We believe traditional law is broken. We want to fix it. We’ve built a one-of-a-kind, scalable technology platform to connect companies with best-of-breed corporate lawyers and make the experience more connected, responsive, transparent and flexible for the customers – and the lawyers.

Juetten: Who are your customers and how do you find them?

Monk: Our customers are companies – C-level executives and General Counsel – generally with revenues of $5 million or more (although we do work with startups as well). There are ~100,000 of these companies in Ontario, Canada alone with an addressable market of $5 billion+ in Canada. We primarily find customers using a database called Zoominfo and outreach cadences through SalesLoft where business development reps follow a recipe of LinkedIn connection, phone call, email, email, phone call, email, email asking for a Zoom meeting. On the Zoom meeting, we connect the clients with the lawyer from our team best suited to helping – and, in many cases, land a new client. We also use telemarketing, paid search, organic search, events and other marketing as a complement to our business development rep efforts.

Juetten: How did past projects and/or experience help with this new project?

Monk: I’ve been a practicing engineer, a practicing corporate securities lawyer, and a business leader with companies ranging from multi-billion international to startup. All these experiences have provided useful learning – above all, that failure often comes from hard work despite all efforts and hopes for a better outcome. The question always is, how do I move on from here?

Juetten: Who is on your team?

Monk: The senior management team includes Rick Russo, a CPA who grew his first tech startup into an exit sale to CGI, a huge tech/software consultancy. Tatjana Monk is our CIO and has over twenty-five years of platform expertise with heavyweights in tech and telecom like Telus and Ericcson. Matt Belbeck is our CMO and has tremendous expertise in legal tech marketing with major players including WoltersKluwer, Reed Elsevier and Ricoh.

Juetten: Did you raise money?

Monk: We’ve raised $1.4 million so far and are well funded for the next 12 months.

Juetten: Startups are an adventure — what’s your favorite startup story?

Monk: One of our earliest customers was an immigrant who had built a successful pharmaceutical business he was ready to sell. He felt overwhelmed by the myriad of issues coming at him and, most fundamentally, his concern over being able to complete the sale without being taken advantage of – by the buyer, by his advisors, or by his lawyer. We connected him with a thirty-plus year lawyer from Canada’s largest law firm who’s been recognized as a Best Lawyer in Canada for Banking and Finance. The lawyer easily was able to complete the transaction while ensuring the client’s best interests were protected and assuring the customer that he was in good hands. And the cost to the client was a small fraction of what he would have paid elsewhere. At the end of the deal, the client wrote me a very sweet note to say “Thank God I met your lawyer, Mr. Robert MacLellan.” This memory is so gratifying to me – proof that we’re succeeding in our mission to fix a broken legal system and deliver something better – for customers and for lawyers.

Juetten: How do you measure success and what is your favorite success story?

Monk: We have big ambitions to reach as many customers as possible out of our belief that we offer a fundamentally better solution for legal help and support. Our goal for the next 4 years is to reach 10,000 companies in Ontario alone served by 1000 lawyers. Currently we serve hundreds of companies with 35 lawyers so we’ve got plenty of wood to chop!

A key measure of our success as we grow is the Net Promoter Score (NPS) we receive from our customers. The best companies in the world for customer satisfaction – think Apple, Amazon, Netflix – have a NPS around +70. That’s our goal and we’re currently close, at +64. What’s great about NPS is that you can compare yourself against players in your space. In North America, the 2020 NPS average for law firms is +26, so Big Law is +26. And we’re +64. That’s success.

Juetten: Any tips to add for early-stage founders?

Monk: I say to founders that their venture is “their baby.” And I say it quite deliberately.

No one will love your baby more than you – and you shouldn’t expect them to. Not your team, not your investors, not your customers, your spouse, your family or your friends. They will support you. They will hope for your success. But no one believes your vision more than you.

So accept that. And then lead others to share your passion knowing that they may come to love your baby too – but never as much as you!

Juetten: And of course, any startup horror stories to share?

Monk: This is not an IP story – it’s just a horror story for me. An early funding effort had us pitching to a pre-screening group of an angel group where I’m also a member. I was certain that, at the least, we’d get the benefit of their time and attention. Instead we met with entrenched views and an unwillingness to listen. The group of “experts”, who I previously had respected, dominated our 15-minutes with explanations of why were are sure to fail and then rejected us unceremoniously. I have a bitter view of so-called angels now and advise startups to be very wary and plan for better sources for funding. In our case, we quickly landed a much larger debt financing on very favorable terms with no dilution of our equity. So the horror story ended with a silver lining, and I’m grateful I don’t have those would-be investors as part of my company!

Juetten: What’s the long-term vision for your company?

Monk: Help people. Fix something that’s broken.  We’re called C-E-O Law for a reason – it stands for Customer – Employee – Owner.  It’s my long-held philosophy that great companies please people in this order. First, you focus on happy Customers.  To have happy Customers, it’s essential to have happy Employees.  Owners come last.  My view is that the best way to ensure happy Owners, is to ensure happy Customers and Employees.

Big Law operates in the opposite way. The firms are built to deliver maximum benefits to the Owners – the Partners. Employees are grudgingly tolerated – and the lower in the pecking order, the more grudgingly. And Customers are treated badly – paying way too much for services that too-often are sub-par, especially if you don’t spend $1 million+ in legal fees each year.

As I said at the outset, traditional law is broken. We want to fix it: Ensure happy Customers.  Ensure happy Employees.  And along the way create happy Owners as we tap into a $5 billion addressable market in Canada alone and build an enterprise with a market value >$100 million in 4 years.


Exciting times for delivery of business law. Here in the U.S., I work with similarly-minded CEOs of legal companies that are laser-focused on changing the delivery of legal services to be client-centric. Particularly with almost every small to medium-sized business facing a multitude of legal issues, it’s critical to have affordable solutions from professionals. #onwards.

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