Meet A Minnesota Tech CTO: Steve Brain, Drip



Thank you Tarmac for underwriting our Meet a Minnesota CTO series, where we get up close and personal with Minnesota’s chief techies!

Steve Brain is the newly named CTO at Drip, which is now a separate company from Leadpages.

How long have you been working in tech for and what is your technical background?

I’m now at 28 years working in tech—23 years of it in technical leadership. However, I started programming at 11 years old and published three books on programming in high school, so “working” in tech is longer than that. I used the high school time to fund skiing
despite growing up in South Wales.

Proud to say that despite this, I never used punched cards, COBOL or Fortran. ;-) I professionally started on the Mac & Unix with C++ & Smalltalk, distributed systems and both relational and object-oriented databases. Then, I progressed through large-scale transactional Java systems on Wall Street. Worked at Amazon for 7 years immersed in micro-services.

These days, my personal technical projects tend to be Go or Node.js.

What are you focused on right now?

I’m focused on building incredible products for our customers at Drip and Leadpages. I have a passion for innovating on behalf of our customers, deep experience in ecommerce, and I am excited to empower businesses to compete. Technology helps level the playing field and give small businesses the opportunity to compete with the companies.

What are the some of the technologies within your company and IT environment?

We have a diverse IT environment. Our Leadpages product is predominantly Python running on Google Cloud. Our Drip product is predominantly Ruby on Rails, though with some new services being built in Scala for scale. Drip leverages Amazon Web Services. Front-ends for both are mostly JavaScript, with new development leveraging React. However, we are building a major new feature in Elm and are excited to see how the benefits of compile-type checking play out. I’m in favor of finding the right tools for the right job and keeping a close eye on innovation.

How do you ensure that IT plans, projects and objectives are aligned with business outcomes?

My role encompasses Product, UX & Engineering leadership. Aligning the Product roadmap with the executive leadership, sales and marketing function can be a challenge. I like to work with “apertures.” That is, defining a customer segment and iterating on features and functionality until we are consistently the best option for that segment. This way you can launch features and measure impact until you know you have nailed it. Within an aperture, you can use Agile techniques, but it’s important you are truly agile (deliberate small ‘a’) as you do this.

What is the size of your department (headcount) and how is it organized/managed?

We’re approximately 45 people split into the two products. In each product we have product management, UX/design and engineering. I’m a big fan of having the three disciplines collaborate together—product represents the voice and need of the customer, UX/design ensures we have an end-user experience commensurate with a modern workforce who demand Apple-like simplicity, and engineering is the people who get to architect and build the solution. Definition of any solution requires all three perspectives to work collaboratively and creatively, both simplifying and innovating.

How does your company approach recruiting and retention for technical positions?

We’re looking for smart, engaged and collaborative engineers. We have our own in-house technical recruiters because engaging talent and providing a great interview experience is critically important. We recognize that technical professionals have many choices, and we want to attract and retain the best. In terms of retention, we offer engaging work, opportunities to learn new things, and a fantastic culture. I was personally attracted to the role based on the strength of the senior leadership, their willingness to make work fun, and the ability to have an impact and the commitment to grow together. Startup life is a journey— you want to be deliberate about who you go on that journey with.

How do you personally keep up with the ever changing technology landscape?

Great questions. I coach so many technical leaders who struggle with this. I have two answers:
I’m constantly curious about what I can learn from my own teams. For example, I learned about Go lang from some of my engineers at a prior company. Right now, Drip is building a major new feature in Elm, so I’ve been really curious about Elm.

I pick side projects to do in my own time to learn new technologies. Both my kids ski race, and the calculation of ranking for the end of season Regional championships is deeply complicated and most parents are totally confused by it. I’ve written a website to calculate these rankings, and over the past 3 years have re-written it in Scala, Node.js and Go. Next season it will be in Ruby on Rails with an Elm front-end.

What excites you about where technology is heading?

I love that consumer software is having such a huge impact on business software. The expectations brought to us in our everyday lives are raising the bar on customer experience for work software. Drip particularly embraces this. We want to make digital marketing super easy yet powerful for ecommerce customers.

I also am excited about the power of properly applying artificial intelligence. There is little truly new in AI. I wrote about it 30 years ago, and much of the “innovation” today is marketing. However, what is happening is creative application with the wealth of data available.

What concerns you about where technology is heading?

There are definite privacy concerns about data usage. This is a double-edged sword. On one hand, abuse of data privacy has been very much in the news. On the other hand, an overly restrictive data policy could stifle innovation. It’s going to be interesting how this settles over the next 5 years.

What is your opinion of Minnesota’s tech industry – how could it be better?

I’m new to the Minneapolis tech scene, but I have been really impressed with the people I have met so far. We have some great local talent. I am seeing some differences in talent and technologies versus other markets, for example in Seattle and Utah. One way I’ve improved the talent working for me is to build development centers in different locations and cross-pollinate experience, technology adoption, culture and learning. Everyone wins in those kinds of interactions.

What are you into outside of technology?

I love the outdoors, which is why I moved to Park City, Utah 6 years ago. Both of my kids ski race, and I love skiing both at the resort and also in the backcountry. I’m also a passionate mountain biker.

Is there anything else you would like to add?

Looking forward to exploring the Minneapolis tech scene. Also enjoying the summer time there—each of my visits so far has been accompanied with a huge snow storm, which is a blessing I wish I’d brought to Utah this winter (we had a poor snow year to our chagrin).