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As the CEO of an early-stage legal tech company, I always wonder what is the right way to build my company into a unicorn. Luckily I was invited to attend the Clio Conference in Nashville TN, a massive technology conference with over 3000 attendees.

I spoke to Clio’s CEO, CTO, head of global sales, and head of digital marketing to find out some tips, and I asked them questions that I had as an entrepreneur. I’ve put the key points into this article to help you with the running of your company.

And if you are looking for investment opportunities in the legal tech space, or just want to learn more about Clearway, go to our investment page.

Dealing with stress as an entrepreneur

I had a short but meaningful discussion with Jack Newton (the CEO of Clio) before he gave his closing keynote. The main thing I wanted to know was if Jack Newton found running a $2B company stressful, and if it was more or less stressful than running a start-up.

He said that running a double unicorn was just as stressful as when Clio was worth $2 million as a start-up. The stress level is the same, but the job and his day-to-day tasks are completely different. Not delivering as a multi-billion-dollar company would hurt an entrepreneur as much as failing as a two-million-dollar company. Entrepreneurs put their heart and soul into the company and treat it as a child. There’s no other way.

As the CEO of Clearway Law, I was relieved to hear that running a unicorn is as stressful as running a startup. If Clio is 1000 times larger than Clearway, I couldn’t imagine how to cope with running a unicorn if it were 1000 times more stressful than it already is.

Jack Newton and Alistair Vigier

Photo: Jack Newton and Alistair Vigier at Clio Con Nashville

Jack was running on four hours of sleep throughout the conference, as his day ended at around 1 am and started at around 5 am. Talk about working hard and giving it your all!

How to scale the tech team

I spoke with the CTO of Clio, Jonathan Watson, about how to run a technology team and build the company culture. Jonathan Watson has been with the company for five years and manages around 300 people in the tech department. When he first joined, the CEO Jack Newton was running the tech department and the entire Clio team (not just the tech department) was 300 people.

Jonathan said that research and development organizations or departments can be hard to manage. Tech people are highly paid and very skilled. If at any time they don’t like what’s going on at the company, they can just leave and get another job. There needs to be a connection to the mission, visions, goals, and people around them, otherwise, they can leave and join another company.

scale legal tech

Photo: Jonathan Watson/ Clio

Jonathan Watson said that even he could leave Clio and get a higher-paying job somewhere else, everyone in tech can. This is almost always true, except for maybe around 2008 when there was the Great Recession.

Leaving for a higher-paying tech job

Since Jonathan Watson mentioned that tech people can leave a company at any time for a higher-paying job, I asked him why he stayed at Clio for five years. 

He said that he loves growing companies, as they create a unique form of chaos that breeds the best form of creativity. Jonathan wants to work at an uncommon company, with uncommon people. He doesn’t want to be a part of an average corporation that does average things and creates average products.

Jonathan said that he likes working with Jack Newton and that he’s a great boss and founder. Within the first five minutes of Jonathan and Jack’s meeting, Jonathan wanted to be a part of Clio. This was because Jack Newton is a product and tech guy that is consumer-focused. There are CEOs that create work, and there are CEOs that do work, and Jack is a do-work kind of guy.

It’s important to craft the why for your staff, why they do what they do. CTOs should not put barriers in the tech team’s way. As a leader, you must make the “right thing easy.” An example of the right thing would be if a tech member needs to fix a bug, it shouldn’t require running it by ten people. If they see a bug, the tech person should fix the bug, and then call the customer and tell them it’s fixed. 

Robert Simon

Photo: Robert Simon, a famous lawyer from Los Angeles at Clio Con 2022/ Alistair Vigier

As a $2B company, Clio pushes updates live around 80 times per day, which is unbelievable. They always have new code that is always going live on the website. The ability to deploy updates and new products using speed and velocity comes from hiring great tech people and good site architecture.

When you start building your tech team, you need to hire devs that have a good idea of the best foundation to use, and what trade-offs to make. Companies should not spend millions of dollars on things that don’t matter, like trying to prevent the website from going down for a few minutes.

Jonathan does start-up coaching both internally for Clio, and externally as a consultant when he has some spare time. He enjoys managing CTOs and tech leaders. Some key advice that he has is to build a business and not a tech platform. The entrepreneurs that build a tech platform don’t tend to make it.

The entrepreneurs that cut corners and make trade-offs in service of their customers win hands down. A lot of early employees should be able to have that, as they have easy access to the CEO. As the company grows, you need to find a way to maintain that culture, given that employees are now more removed from the CEO.

As a CEO, you need to say the same things so many times to get a point across. You will need to talk constantly about being customer focused. Once you get tired of saying it, say it some more.

Grand Ole Opry

Photo: Part of Clio Con 2022 took place at the Grand Ole Opry In Nashville/ Alistair Vigier

How To Build Your Technology

When building your technology or hiring a tech team, you shouldn’t start with what tech stack you want to use. It’s important to start with the customer’s problem and work backwards from there to figure what’s the best way to solve it using a tech stack. React, Ruby on Rails, and Javascript are good options.

When hiring tech people, it’s best to be open to training web devs to learn your tech stack. You want to find people that want to continue to learn. Don’t only look for devs that have everything up front, that’s hard to do.

Jonathan’s main tip was to make the right thing easy for your team.

Building your sales team

I spoke to Jenny Dingus, the Senior Vice President of Global Sales at Clio. She worked in sales for RingCentral for ten years and now leads the sales team at Clio. She started selling on the phones as an agent and worked her way up through the ranks at RingCentral. The company quickly grew, and Jenny grew with it.

She left Ring-central for Clio because she wanted to be head of sales, work with small businesses, and wanted to have a company that was willing to invest in strong infrastructure for the success of the sales team. And Clio checked all the boxes and Jenny made the decision to go forward. And everything that Clio promised Jenny during the headhunting process came true.

scale legal tech

Photo: Jenny Dingus/ Clio

When Jenny Dingus saw 2000 lawyers attend Clio Con 2022 in Nashville, she felt her decision was validated after seeing how successful Clio was, and how happy the customers were. Clio has an obsessed customer base which is almost cult-like. Most companies dream about having a customer base that shouts from the rooftops about how great a company’s product is, and Clio has that.

It’s much easier for a sales team when customers know they should do something, versus having the sales team try and convince them.

Most lawyers know that they should be using practice management software. The question becomes if they should use Clio or their competitors. And that question is what the Clio sales team focuses on.

Clearway was also on-site to connect with people!

Jenny sees the job of Clio’s sales team to not push sales, but instead to act as consultants to law firms. 

When it comes to selling a product, not everything has to be perfect for a company to be a valuable solution. Salespeople and entrepreneurs need to understand the people they are talking to and work to make their lives easier.

Hopefully, you can use some of these tips to scale your own legal tech company and become a success story like Clio.

Author: Alistair Vigier is the CEO of, an online legal marketplace.