Upon joining BetterCloud as its new CTO, Jamie Tischart was taken aback when he reviewed his professional biography with a colleague. “The first line was, ‘With almost three decades in technology,’” he told me. “And my reaction was, ‘Has it really been that long?’”
In the 27 years since he began his career, Tischart has quickly risen through the ranks. He’s held executive-level engineering positions at companies such as Intel, McAfee, and SendGrid. Before joining BetterCloud, he served as a VP of engineering at Twilio.
We sat down with Tischart for an informal, but wide-ranging discussion about software development, management philosophies, and the future of engineering at BetterCloud.
Editor’s note: This transcript has been edited lightly for clarity.
I’d love to hear more about what excites you about the opportunity here at BetterCloud.
I just see the opportunity that we have in BetterCloud. One of the things that we all complain about is the systems and processes across all of our companies. BetterCloud is a company that’s going to solve that problem in a big way for all of our customers.
There’s an incredible amount of optimization and automation that we can do as an organization that will help all of our customers be more successful. At the same time, this is an area that has been underserved from a technological solution set. When it comes to leveraging automation and development capabilities to solve problems, our industry is one of the only remaining laggards.
Finally, when I left Intel to go to SendGrid, I was excited to join a smaller organization and help them mature. I was very successful at that and I am eager to do it again at a company like BetterCloud.
With every opportunity, there are also challenges, right? What are some of the biggest challenges that you’d like to tackle as the company’s new CTO?
I think there are a couple of things. First, I think it’s really important to create that engineering identity and help the entire organization understand the challenges of software development.
It’s easy to say, “Well, let’s just go build things.” But you are working on a system that generates millions in revenue from thousands of customers, all of whom have certain expectations of the product. That’s something people tend to underestimate. It takes a lot of work and effort to manage those expectations while also building new things on top of the existing product. So I think we need to educate folks about what engineering does, how we do it, and why we do it. Once we do that, it’s important to set expectations for ourselves around how we can do things better. This is going to be a huge business, but we’ve got to think about where we’re going and be intentional about what we’re doing and what we’re building.
The other thing I’m thinking about is removing obstacles so that our people can do their best work every day. How can I enable them to do creative and complicated work without having constant shifts in priorities and mind share? I preach a lot about developer velocity and how to protect our engineers’ time so that they can do thoughtful work, which helps us be a lot more efficient.
The creativity piece of that is really interesting, especially when you think about building engineering teams. How do you balance the need for engineers who know the organization’s current tech stack with the reality that a talented developer might need to learn some of those languages on the job?
It’s a very complicated problem. I always say that there’s the fallacy of the full-stack engineer. We think that very complicated disciplines can be fully realized by any single individual. So what I am looking for always in the talent on the team is people who are open to learning and exploring new things; I think the team should have a wide breadth of expertise and knowledge. The team should have all the pieces that it needs to be successful, but no single individual has to have them.
That’s how I’ve approached it, and it has been relatively successful. But the only thing that you can count on is that everything is rapidly changing. So if you’re not careful, you can get into a mode where all you do is evaluate new technologies, platforms, and tools. I like to say, “Today’s tool of choice is tomorrow’s tool of complaint.” Once you’re good at one, then you find all the problems with it and start complaining about it—and that’s pretty much the case with anything that we have to select from a technical perspective.
Speaking of evaluating new technologies, are there any “emerging” programming languages right now that you think might be an essential part of a developer’s toolbox in a couple of years?
At some point, I think every engineer is going to have to embrace machine learning and possibly some of the open machine learning libraries, like OpenAI. We have to embed intelligence across every part of our technology and our stack. We’re all dealing with so much data, so much complexity, so many opportunities to simplify and recommend solutions. The more machine learning that we can build in to support that, the more competitive that we’re going to be.
As far as just languages or tools, it depends. Once you understand what you’re trying to solve for your customers, then you can start asking yourself what the best tools are for those specific problems. I look for what is the most scalable and reliable. I think almost all languages can serve the purpose that you need. What it comes down to is whether it’s fueling the continuous growth of your engineers. More importantly, is it also fueling the delivery of value for your customers?
In my conversations with software developers, it seems like there are two career tracks: Either you code for your entire career or you eventually move into people management. So what inspired you to go in the management direction? And do you miss sitting down and getting into the weeds of a codebase?
One of the reasons that I went into management is that I got a lot more energy out of solving human problems than I did technical problems. And quite frankly, I was not a great engineer. I’d solve something in 100 lines of code, and then a colleague would go and solve it in 20. For whatever reason, a big part of my core is doing things efficiently.
Now, I love sitting through code reviews still and I will do that quite often. But what I was good at when I was an individual contributor was thinking about more simplified ways to approach problems. So now I get to spend my time looking at the trends and identifying different ways to solve problems.
I’m going to pivot us back into a BetterCloud-specific question. Obviously, the cloud is not new to you. But how might your approach to management or engineering strategy change to serve the needs of our customers?
I think one of the things I talked a lot about in my career is how people were always really concerned about cloud security. The reality is that most companies don’t do security well. The providers you work with frankly do it better than you can do it. That’s not to say that doesn’t come with risk. You’re putting a lot more of your business into the hands of others. But ultimately what it allows you to do is focus your resources and your talent on your biggest business priorities.
In five to 10 years, I think we’ll start to see more trust in machine learning data models to do more things on our behalf. We can leverage a lot of data from a programmatic and modeling perspective, but the trust isn’t there yet. That’ll be the next barrier to cross. Security was the barrier to using more SaaS applications and cloud services. The next one is convincing customers to let us use the information we have to make decisions on their behalf.
There’s still a healthy distrust of data collection and utilization. I personally believe that we can do better as a community to alleviate this distrust by providing transparency around data utilization and how it provides amazing value for our customers. And I think that’s a huge opportunity for BetterCloud. We can leverage what we know and how we know it to make recommendations and proactive behavioral impacts for our customers.
That’s incredible. Just one more question: What hobbies are you looking forward to enjoying again when the pandemic is over?
I haven’t seen my parents face to face in two years. They’re both over 70 now, so I’m looking forward to going and spending some time with them. But also, my wife and I were planning on doing a month-long New Zealand, Australia, and Fiji tour to celebrate our 30th anniversary. I’m missing traveling and exploring new places. That’s one of our favorite things to do. So other than going and visiting everyone, and getting to meet everyone face to face at BetterCloud, I’m looking forward to that month-long anniversary vacation at some point in the next 18 months.