CTO interview: Jonathan Watson, enabling the tech behind the stellar Clio
I chatted with Jonathan Watson, CTO at Clio, a global leader in legal technology. Clio helps lawyers run their practice, improve legal workflows, process legal payments, and much more, with the largest API in the legaltech space that connects to more than 200+ applications. Jonathan was promoted into the executive suite this year as Clio’s first CTO, setting course as the company expands its centralized suite of products. In this interview he muses on leadership philosophy and challenges of the job, while offering his take on details like the pros and cons of monolithic code and microservices. He also discusses how Clio handles the intense privacy measures required as it handles confidential information from multiple countries.
You’ve had an impressive career. Can you please share an overview on how one becomes CTO of such a successful company as Clio?
I got into tech a bit later in life. For the most part, I didn’t program — except for a bit of PHP in high school — until I moved to California and gave it a shot trying to become a dev.
It took a bit of time learning the ropes prior to the rise of bootcamps to help people learn the practical aspects of the work. I quickly recognized my skill set was really behind what was needed to become successful. I asked a lot of ‘stupid questions’ for the first three years of my career as a dev. I found my stride with a technical mentor helping with high availability, scalability, code review, etc. I followed him to the Bay Area, still asking loads of questions. I ended up with a director of engineering who saw a lot of potential in me and, eventually, in turn asked me how to approach some things.
As a leader, I was always curious about why we did things a certain way. Eventually I went to Shopify, a company I didn’t really know at the time. It was financially rewarding and I got to work with cool people, but I wanted more context to my work, to develop faster, and to zoom out to how decisions were made for impact. Then Clio popped-up on my radar. At the time, it had a dev team of about 50, and Jack [Newton], the founder, wanted to grow it fourfold. I had led, at maximum, maybe 130 people, but never scaled to that degree, or been part of an executive team.
I embarked on that journey almost five years ago, handling data privacy, compliance, and data engineering functions. The eventual move to CTO made sense as I was doing a large portion of the remit of the company. I picked up design and product along the way.
So what were you doing before developing?
A lot of different things. I did IT stuff like running network cables in hospitals. I also set up software for a medical software company and trained people on it. I still remember the Windows 2000 CD key — it’s imprinted in my brain. I opened an internet café and became a professional gamer before it was an acceptable way of living. I even did some carpentry and construction — really anything that allowed me to be hands-on to build, solve, organize, create — all of which are still highly relevant to the work I do today.
What are the biggest technical challenges you’ve encountered?
A broader issue that results in a lot of technical challenges is the red hot job market for engineers. It has resulted in a lot of mobility to switch companies. You have to onboard folks fast and deal with the inevitable challenge of brain drain.
Clio’s heavy investment in culture is especially important in this environment.
How do you balance the growth and cleanliness of your codebase with a high growth rate company that’s trying to innovate?
Managing a product as wide as Clio in features and scope, with a wide range of customer profiles from solo players to enterprise levels, means we’re building a centralized product for a very wide variety of needs.
I think a lot of early cloud companies are facing this challenge at this stage of growth and maturity. Scaling Clio on our codebase takes meticulous maintenance and updating, a constant challenge for us to set our foundation to meet an expanding list of needs.
What technologies do you use to build Clio?
Primarily Ruby on Rails, also some Python and Django with Go. We’re monolithic by nature, although we have some microservices. For example, our billing system is a service because ultimately there are compliance and regulatory requirements when moving and reconciling money. It is small scale to manage, as opposed to handling it as part of the main codebase. Both monoliths and microservices have upsides and downsides; you just need to pick what’s right for you.
How do you handle data privacy considering the different legislations in the US, Canada, and Europe, where you operate?
Everything is the same codebase, and we put as many boundaries in the cloud as we can. Data security is our largest priority — full stop. Lawyers’ and clients’ data is absolutely privileged; we don’t want to see it or engage with it. Only a few people in the company can access it and they are tightly monitored to fully filter access to that data.
What about backups in different regions?
At Clio, we prioritize the resilience and availability of our customers’ data by hosting data in physically disparate datacenters and storing backups in geographically diverse areas. We also optimize for the accessibility of that data by ensuring that it can be returned from those geographically diverse areas into service in our production environment with a very low latency.
We believe in privacy regulations that create more complications. Application servers run the code in different regions, but databases and caches are region specific. Despite this, the codebase is unified, and we deploy frequently.
At Kolleno, we integrated with Clio, and we’ve been impressed by how responsive your team is and how quick changes can be implemented. In terms of becoming a central platform, attracting developers building around the Clio product, what is your strategy?
Our application ecosystem is very important to Clio, because it helps lawyers who may have different firm sizes, practice areas, and jurisdictional regions build on Clio something highly specific to them. It also generates a lot of innovation in the technology space. Clio’s mission is to transform the legal experience for all, but that doesn’t mean we have to go it alone. We have a fully dedicated team to maintain the Open API and find innovative embed applications. This helps take a load off the start-ups and smaller folks that we can handle with our scale.
Next, Clio should be the centralized data store for everything. We’re working to make that simpler and more apparent to developers. We have a developer outreach team, too, and we’re trying to get more people on the platform to see the value.
We want to ensure that if you build something, Clio will help your business scale rapidly. We want to create that true synergy of two companies building their businesses together and serving each other’s needs.
Do you have any advice for younger people starting their career?
I do have advice, but will say it’s very much steeped in my own experience and privileges. I recommend asking ‘stupid questions’, but only ask them once. Find a way so you can feel safe doing that. It takes a lot of work for some people. For new folks, don’t think too much of getting it right the first time. Get curious, and you will grow way faster in your career.
Do you have a fun fact or horror story that you’re willing to share?
I’ve got a few. One that comes to mind is a very interesting app partner at a company I worked with. They were effectively DDoS-ing us over time, and unwilling to change their software, which had that unwanted side effect. We couldn’t just shut them off, so we had to find a workaround. It was an interesting problem for about a week: identify traffic that is by nature unidentifiable. It was a super fun time in retrospect.
If you want to connect with Jonathan, click here.
To learn more about Clio, visit their website: clio.com
If you’re a techie working on something exciting or you simply want to have a chat, get in touch with me. I’m currently CTO at Kolleno.com
FROM THE AUTHOR
>> 5 reasons your invoices are being paid late
