Remote Work and Team Success with Brien Colwell

In each HeadSpin Corner episode, our VP of Developer Products Jeena James talks to experts and thought leaders at HeadSpin and in the industry about what’s new in both the testing community and digital experience space, the latest industry trends, how to achieve digital business success, and more. You can find more episodes here.


Our guest for this interview was none other than Brien Colwell, our Co-Founder and Chief Technology Officer. Before HeadSpin, Brien founded a Y Combinator-backed startup called Nextop and led the Android team at Quora. He was a lead engineer for several other startups as well, so our conversation spans entrepreneurship, remote work, and engineering team success. We talk in detail about his journey from being an engineer to a tech leader, his approach to building an effective and collaborative engineering team, and his commitment to customer success.

Read on or watch our interview below to hear our discussion on startups, remote work, and team success. 


Tell us a little about yourself and an app that you absolutely love right now.

Starting way way back, I graduated from UC Berkeley EECS, coming out of that with info business as my focus area. I did a bunch of undergrad research in information visualization and then went into Silicon Valley. I spent a brief time as a researcher after that but realized that I love building products and getting stuff that people use. I find it very satisfying and I’ve just been working at startups ever since.

I really love communication apps. In no particular order, I have Slack, GitHub, BlueJeans, Zoom, Dropbox, and YouMail. I think these are all really interesting communication apps helping me stay in touch. I really do love this segment of apps and personally I use iMessage and FaceTime a ton to keep in touch with family and friends.

Before HeadSpin, you were at Quora. Tell us a little more about how that experience was and how it was to work with Adam D’Angelo.

Adam’s one of the smartest people I know. It’s really awesome to see him work. He wasn’t really in an engineering role at Quora, but certainly is a founder in setting the direction and it was really great to interact with him on a daily basis. He’s currently an investor in HeadSpin, so it’s great to still have him on the team here. One of the most interesting things about Quora and one of the reasons I was interested in joining is that it really had a long-term mission and idea of how to make data useful. I think there’s an intentionality about how you approach building a platform that creates data that sort of turns ML models and builds a long-term impact in the ecosystem. Adam was very intentional about it and it was very inspirational to see his thinking 10 years in the future. I think a lot of those lessons have really inspired me, my future work with data, and my current work with HeadSpin.

Where did you go after Quora?

After Quora, I joined a small start-up. I really wanted to get involved in future-of-work communication. I had an opportunity to work with the former CTO of Microsoft. He started an app and I joined as his Android lead building out this Android app that he was working on. It eventually got acquired by Microsoft, shut down, and became a part of Microsoft Teams. We were contemporary to Slack and doing this momentum of trying to reinvent work communication. Based on that experience, I had a lot of thoughts about how to build apps. Going through Quora, I was definitely able to launch more apps to global users, get a lot of learnings about supporting apps, how to build great apps, working with users to fix issues, and iterate on apps. 

My other experience is actually much more how to build a robust app, how to build a reliable app, because it was a communication product. Through that, I think I really found it interesting that I had sort of come into the mobile space in around 2010, and was trying to learn my background up until that point was data enterprise and data systems and was learning a bunch but really felt like I was like learning like every day and every week how to handle a lot of different variability in the way people are using apps. I thought that it was interesting to me that a lot of apps were using a relatively small number of open source components, and I wanted to go off and try to make the network experience easier and better to build more reliable apps. So, I started a company called NexTop and that was my “next stop.”

Is that how the name for Nextop came to be? Is that how you named it?

I think it was “Mobile’s the Next Desktop”, so it was the next desktop. Desktop is this reliable platform that’s on Wi-Fi that everyone trusts to do work, and so it was a combination of where’s next desktop and that was Nextop. It was trying to make mobile very reliable, usable, and a tool that people could embed in their apps to fix problems.

Nextop was backed by YC. How was that process qualifying for YC? Tell us a little bit more about it.

That was a fun process. My co-founder and I actually recorded our YC demo or pitch video in a  taxi cab. We rode around New York City and basically showed how apps were working in the cabin and picking apart how they could be done better, but essentially mobile teams just didn’t have time to fix this stuff. 

Basically the YC application is you do a couple of interviews. It’s funny — around the same time we were interviewing a book, Peter Thiel’s book Zero to One came out. I really like Peter Thiel. I had the opportunity to work with him at the first start up I worked at. He’s obviously a really smart business thinker, and I found this book Zero to One really insightful. Apparently the YC interviews also think it’s very insightful, because I felt like a lot of the questions during the interview came directly from Zero to One or similar. I think Zero to One came from a bunch of  Stanford Business School lectures that Peter Thiel had given.

I think YC is investing in companies hoping that one will find some repeatable value that no one else has seen, and so a lot of the questions are: What’s the market opportunity? One, can you go there? A lot of people have ideas, but YC is very much focused on people taking ideas to reality. Can you build it, and then also what do you know? What do you believe that other people don’t know? What are you going to double down on as you build your company, because you can’t keep changing directions every year? You have to commit to a marathon of building value over the next five years or 10 years in this direction of where you think you have an advantage. 

I think what we thought was the network is really hard, from our experience building apps, and also developers rely on a relatively few number of tools to build with, so we felt that the network also impacted a lot of the user experience. We felt the majority of issues that end-users experience was probably due to some network issue, so we felt if we built really good tools to fix the networking side then there would be a business there. 

It would fit into what people currently do and trusting a relatively few number of tools. Our challenge was how do we actually build a business? We knew there had to be some open source and some closed source. I think that was the big challenge for us.

Shifting gears to HeadSpin, how did you meet Manish? Tell us a little bit more of that journey, and how did you realize Manish is the co-founder you wanted to work with? Tell us how that relationship has evolved over the years and some of the things you’ve learned together.

It’s funny when people talk about Silicon Valley. It’s kind of an idea, but I do think that there was something special in Silicon Valley right? I started my career as a little start-up in a basement on PageMill. So, it’s funny 15 years ago, I was in a basement on PageMill, and then fast forward to 2015, and I’m going through an extended seed round talking to VCs and trying to think of what’s next with a company and where we want to take this company. Obviously I had a lot of thoughts about a different way to sell it than an SDK. We needed to be a platform or something that tapped into other types of budgets.

One of the companies I pitched was AME Cloud Ventures. Our current office happens to be It’s two doors down from AME Cloud Ventures. I pitched to Nick Adams over at AME Cloud Ventures and he said look, I’ve heard this before. Somebody else is trying to start a company trying to build some kind platform where you can fix issues in your apps, and you should go talk to them. Silicon Valley is all about creating win-wins — the mutual win between the founders and the investors, everyone in the company, all the shareholders working hard and coming out on top. I think it’s really magical to see it happen where you can pair up with someone who can accelerate what you’re trying to do. 

Nick made the intro to Manish, talked to Manish, kicked around some ideas. I felt there were a couple things that really impressed me. One was that there’s a lot to build here. We’re five years in here at HeadSpin, and there’s still a lot to build and a lot to go. That was pretty apparent that we’re talking about something that really hasn’t existed before in terms of a testing platform, a monitoring platform, a data platform. It was very exciting to me that we were touching on new topics.

Additionally, what I saw in Manish was commitment to customer success, and I think we both wanted to work very closely with customers to make sure customers succeed and can get some value. I think it’s that iteration with customers that we’ve been doing ever since we’re a super customer-driven company. We work very closely with customers trying to build the platform that works well for them. Manish has started companies before and everything you have to do as a founder, Manish embodies you have to get products out fast, you have to find out what your advantage is, think on your feet, act quickly and build things quickly. It’s been great working with him, working with customers, and making this into a real company. I think we’ve gotten there, and it has been very exciting.

You constantly bring our conversations back to stability and reliability of the platform. What does that mean, and how have you been building it with the customer voice in mind? How are you scaling something like that as hundreds more other customers and channel partners access our platform?

This is all a part of our journey in our evolution from a start-up to an enterprise-class company. Great companies and great products are products that you can trust, that you believe in, that you can recommend to people, and that solve problems reliably for you. From a company-side, it’s the difference between a nice-to-have product and a must-have. If you’re something that people can rely on then you take a lot of pressure off them and you make their lives easier. Building a company that can deliver that type of stability, reliability, and enterprise trust for customers is something that’s very important to me. Everything I do, I keep that in mind.

As a team, we see ourselves building something at the class as AWS. EC2, which is something that a lot of companies trust AWS with. You wouldn’t think twice about spitting up an EC2 instance and using it for something critical to your business. That’s the level where we’re taking HeadSpin, and everyday we review and improve how we can make this so that companies can set up their automation using us and run it and trust that it’s working correctly and get the data they’re looking for. On our side, it’s making sure the data is continually accurate and that the infrastructure’’s working at the SLAs that we expect. When we built HeadSpin, we knew this was going to be a different type of data center and infrastructure.

When you talk about having a giant global platform and that’s going to be the essential piece of your platform to be able to access so many different locations in the world — you really have to approach that from a different perspective in terms of how you build that type of infrastructure and that type of data center. I think at our very core of the company is we’re building a data center a big distributed data center. Everyone expects a data center to be reliable, secure, and enterprise-class, and so certainly everyday we continue to push in that direction and make that a reality. I think that’s how great things are built. It’s week over week progress, focusing on a goal, and never losing sight of that goal. We really are very grateful for all of our customers and continue to push to make this a tool that works well for them.

Tell us a bit more about what your guiding principles have been in building out a successful engineering team, a team that is mostly at the Palo Alto office but also in different parts of the world and is very collaborative in person and online. 

Every startup is in a talent war, with the make-or-break of any company as getting great people who can execute. We have a relatively low higher rate. We really look for people who fit with high caliber, high character who can communicate. What I look for in the engineering team is three principles:

  1. I look to work with great people who are driven and who want to build something that matters
  2. I also love to work with people who want to get into the problem: write code, ship products, talk to customers, and repeat. I think that’s what the essential function of product development is; you build it, get it out to see how people are using it, and repeat. It’s a process that never ends. 
  3. I look for people who want to continually improve, and that’s essential in the industry. Anytime there’s a market, there’s always competition. Change is inevitable, especially in our space, where there’s a new release every year and our customers are releasing every two weeks or so, and the platforms we’re releasing on are changing every year. We continually have to improve and keep up-to-date with what we do, and so having that drive in people who are never satisfied and always thirst to make it better and solve the fundamental problems. 

Those are the types of people I love to work with.

As part of the talent war, I think it’s been recognized for a while that when you start an engineering team, you should really think about working in a way such that you can onboard remote collaborators. This actually opens up the ability to hire remote whether or not distributed remote is like a majority of the team or sort of a subset. In this industry, a lot of times you’re chasing talent that’s a good fit. There’s not an abundance of people who are networking experts who can also build native components and do protocol analysis who are looking for a job. A lot of times when you find someone who’s a fit, it really helps to be able to adapt to what where they live and want to work. Nobody’s going to stay at a company where they feel like they’re not able to contribute. 

One of the goals I had for starting the team was that we were going to try to work in a way that could scale distributed remote or at least had a ramp to go there, whether or not I still valued that. We do have about 60% of our team in Palo Alto, but as we grow, we’re expanding up into Canada, New York, Tokyo ― all growing hubs. So, I hope that we can continue to find great people there.

How has Shelter-in-Place affected that, and how are you still driving a successful and collaborative environment?

All of our communication is document-driven in a way such that changes are logged and people can catch up. Every project we work on has a clearly-written goal. We do specializations and then project teams that pull in people across specializations. Every project we do has a goal that’s clear and scoped into timelines that are clear so people can catch up and understand what they’re working on and when someone joins they can quickly understand what the scope and delivery of the project is. 

We have a way of communicating with chat that I think is effective. It lets us keep our communication focused in terms of project teams, incidents, and general teams to keep people feeling connected. Someone on the team has recently tried doing Hangouts on a regular basis, especially during this time, and we do an all-hands every two to three months to make sure we’re on track with our yearly goals. When you’re on the development side of building a product, there are so many things you can build and not all of it matters, and it really helps if everyone on the team has a fast understanding of what matters and what doesn’t. That is very clearly set for the team so that everyone can make these decisions and make sure that projects are allocated in a very controlled and focused way and the project teams can own and evolve the projects themselves. There’s a huge amount of ownership and trust once we decide to work on something.

I think overall if project teams feel aligned and people feel like they can communicate and understand what people work on ― almost everything we do is in Git, because we want to be transparent in how we build our products ― then things can scale and onboarding becomes more successful. So far, what we’ve been doing has been great. 

I’m personally very interested in remote working and think it is the future of work. I actually joined a company before becoming a full-time entrepreneur that was focused entirely on remote working. I think remote working lets people reach a better optimum in their life. I think for me personally when I run an engineering team, I will have a remote-friendly bias to the team, and I think it really involves making remote people feel connected the same way that people in the office are connected. Obviously not every conversation is there, but so long as everyone understands the projects and the product equally. 

It sounds like you prioritize and focus on talent and skills. Location is not the first thing that you’re optimizing for but rather how skilled, talented, and collaborative everyone is, that way you get the best of talent no matter where they’re located. If I were to draw a parallel, that is like being able to test and run performance tests no matter where the device is located. We’re kind of staying true to the platform goals as well. 

Yeah, every startup, especially their engineering teams, are in a talent war. Engineers who can build and deliver can get a job so fast. If someone is a fit and interested in what you’re doing and feels like they can be productive in what you’re doing is a huge advantage for any startup. 

That being said, can you pick a rising star from your team?

I can’t name names; everyone on my team I think is really good. At one point I heard a measure of a successful team or a company culture is how many startups come out of the company eventually. I’m sure you’re familiar with the PayPal Mafia and just how influential that team has been, and obviously PayPal has shown itself to be an enduring product. I believe the same way.

I feel like my first goal for a team is to enable people to be successful with their career and what they’re trying to achieve. I do think that attracts a lot of entrepreneurial people to work with me, and I think that I would invest in quite a number of startups that came out of HeadSpin just based on the people, but I can’t name names, because I don’t want competition. 

That’s such a brilliant way of looking at it ― measuring talent and success by how many successful startups come out of one.

I think this measurement really speaks to the quality of talent you can achieve. A product is a bunch of decisions made every day, and you have to hire people you trust to make the right decisions, because if you make the wrong decisions you eventually just don’t get to where you’re trying to get to. If you can get those entrepreneurial people who can focus and make the right decisions, obviously they’re going to help drive our platform forward and solve these really important problems that we’re trying to solve. Those same skills are the exact same skills that are going to be applied in new domains, and those are exactly the type of people I look for. 

You often work with cross-functional teams. How do you and the team collaborate? Give us an example of anything recent that comes to mind of any initiative where you collaborated with cross-functional teams.

We’re an extremely customer-focused company and design partners have been huge for our success. When we’re able to build a beautiful solution as part of our platform that satisfies the need of a leading company in a space or a partner we think is particularly insightful in a space, that’s huge. We recently launched a pretty awesome new set of features for one customer.

It’s really awesome to see work across the team with sales, customer success, operations, to get the product built and delivered, making our customers successful, and then seeing the product evolve and advance to basically make that process repeatable. I think that’s how product development has to be done. If what works for a leading customer can be repeated for other customers, then that’s how you build something that’s applicable to the industry.

That requires working every day with sales or working every day with customer success to solve hard problems that are affecting customers. The entire team is dedicated to customer success.

I think what I focus on is making new salespeople successful in terms of my role aligning the business with the technology and guiding the company. A really important piece is whether we can onboard new sales people and have them successfully deliver value to customers. Another is how we are supporting our new and current sales people and making the process repeatable for them. There’s a lot we offer, from hosted to on-premise, and making all of these processes repeatable and scalable has been exciting.

What are some of the exciting features that you can share that HeadSpin is thinking about for 2020 and beyond, and what keeps you up at night besides coffee?

What keeps me up at night is pings on WhatsApp. I’m just joking. As for exciting features, what I see is more data and our efforts to offer more data. We have a ton of great data coming out speaking to networking, budgeting protocols coming to the platform, and streaming performance data. Getting more data to customers is super exciting. It helps them make better decisions and increase the value of their automation. 

Running more automation is also huge. We launched an initiative called HeadSpin University to train and give people who don’t know automation a resource to learn automation, and every week we do a live automation of apps. We have some really great apps on the schedule. 

Jonathan Lipps Automation Zoom App on Android

I’m also really excited for the tooling we have around first load and web page testing, which makes it really easy for people to basically get data from their app without any automation experience. The machine learning and the AI issues are super exciting for me.

This year we’ve seen the amount of useful data from every test increase. For example, now when you run a browser test on HeadSpin, it automatically gives you the page load time for every page. You can actually just tap around the page from your test or from manually. We automatically give you the amount of time the page took to load, which is great, and all this goes into our open data platform and our dashboards. 

We also just launched the new awesome regression feature. We’ve been pushing more to make the data operationalizable by teams, such as when you’re running your integration testing continually, how you can find performance regressions and how you can find user experience regressions. There was a ton of stuff that came out last month and coming out in the next couple months around that: new UIs, new databiz, APIs to help you understand regressions. We’re super excited about all that, and there’s other stuff on the road map that I can’t completely reveal, but there is definitely a lot being built. Getting more automation and more data sums it up.

This article is a summary and transcription of a recent HeadSpin Corner episode. You can watch more HeadSpin Corner episodes here, or listen wherever you hear your podcasts.