As the CEO of an early-stage legal tech company, I always wonder how to scale legal tech. Luckily, I was invited to attend the Clio Conference in Nashville, TN, a massive technology conference with over 3000 attendees.
I asked Clio’s CEO, CTO, head of global sales, and head of digital marketing to find out some tips, and I asked them questions I had as an entrepreneur. I’ve put the key points into this article to help you run your company.
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. I wanted to know if Jack Newton found running a $2B company stressful and if it was more or less stressful than running a start-up.
He said 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 daily tasks differ. 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.
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.
Photo: Jack Newton and Al Vigier at Clio Con Nashville
Jack ran 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, CEO Jack Newton ran the tech department, and the entire Clio team (not just the tech department) consisted of 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 they don’t like what’s happening at the company, they can leave and get another job. There must be a connection to the mission, visions, goals, and people around them. Otherwise, they can join another company.
Photo: Jonathan Watson/ Clio
Jonathan Watson said that even if he could leave Clio and get a higher-paying job elsewhere, everyone in tech could. This is almost always true, except maybe around 2008 when the Great Recession occurred.
Leaving for a higher-paying tech job
Since Jonathan Watson mentioned that tech people can leave a company anytime 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 unusual people. He doesn’t want to be a part of an average corporation that does average things and creates average products.
Jack Newton and the legal tech industry
Jonathan said he likes working with Jack Newton, 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 who is consumer-focused. Some CEOs create work, and some do work, and Jack is a do-work guy.
It’s essential 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 it and then call the customer and tell them it’s fixed.
Photo: Robert Simon, a famous lawyer from Los Angeles at Clio Con 2022
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 developers with 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.
Scale legal tech software
Jonathan does start-up coaching internally for Clio and externally as a consultant when he has some spare time. He enjoys managing CTOs and tech leaders. Some key advice he has is to build a business, not a tech platform. Entrepreneurs who build tech platforms don’t tend to make it.
The entrepreneurs who cut corners and make trade-offs in service of their customers win hands down. Many 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 must say the same things 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. This is how to scale legal tech.
Photo: Part of Clio Con 2022 took place at the Grand Ole Opry In Nashville
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 essential to start with the customer’s problem and work backward to determine the best solution 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 developers with everything up front; that’s hard.
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. As an agent, she started selling the phones and worked her way up the RingCentral ranks. 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 have a company that was willing to invest in strong infrastructure for the sales team’s success. Clio checked all the boxes, and Jenny decided to go forward. And everything that Clio promised Jenny during the headhunting process came true.
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!
Scale your legal tech company conclusion
Jenny sees the job of Clio’s sales team as not pushing sales but instead acting as consultants to law firms.
Not everything has to be perfect for a company to be a valuable solution when selling a product. 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.
