Tech Leader Spotlight: Matthew Boeckman

Tech Leader Spotlight: Matthew Boeckman 

via Twitter. 

via Twitter. 

During Denver Startup Week, I had the chance to sit down with Matthew Boeckman. Matthew is the Vice President of Infrastructure at Craftsy, leading a cross-disciplinary team of devops, database, QA, internal product development, and IT help desk engineers. Outside of Craftsy, he’s passionate about giving back to the tech community, bringing teams together, and his landscape pond.


What is your involvement in the Denver tech community?

I’ve been in Denver for 9 years in various roles at both large organizations and startups. I try to speak at events like Denver Startup Week and meetups around the city as much as I can; and mentor the people I’ve met along the way.

Additionally, I am an executive sponsor for meetups at Craftsy, where we host a devops meetup and an Amazon Web Services Cloud meetup. Overall, I try to be an active member of the community and give back with the resources we have.

Why Denver?

I’m originally from the middle of nowhere Kansas, so I spent the first 10 years of my career in Kansas City. About nine years ago, my wife was looking to get her MBA and after looking at schools all around the nation, we decided on CU Boulder. They’ve got a great entrepreneurial MBA, which is what she was looking for. Plus, I knew Denver was a good fit for me because of this fantastic tech community. I wanted a location that allowed me to grow both as an entrepreneur, engineer, and leader of engineers, and Denver is pretty perfect. 

What is your favorite part about the Denver tech community?

It’s a combination of things. First, Denver has an incredible access to talent. Over the last 20 years, the city has been a hub of technology--first in telecommunications, then storage--so there’s a great braintrust on those two. Then, with the increasing amount of venture capital investment in the community, we’ve created a self-perpetuating cycle where we are able to both attract and retain top talent.

I also love how open and engaging the Denver tech community is. Whether you’re part of a large or small organization, something about Denver gets people talking, which is really how we learn from each other.

If you could change one thing about the Denver tech community what would you change?

I would make it a little less popular. I do a fair amount of recruiting in my role at Craftsy, and if you’re trying to bring candidates in from other places in the country, Denver property values are a real barrier to overcome. It’s a fantastic community, but the location is getting almost a little too popular.

Outside of your work at Craftsy, what projects do you like working on for fun?

Outside of work I try to get away from tech; I spend plenty of time in front of a screen at work. So, I have a nice landscape pond I enjoy working on, as well as a very active family life.

What is your workspace like and why do you like it?

I spend most of my day in meetings, but we have a pretty good culture of walking meetings and getting outside when we can. When I’m not in a meeting, I sit in a big pod of desks--Craftsy has an open floor plan. So, my workspace is really a hodgepodge of a shared desk, comfortable seating, meeting rooms, and then just walking around downtown connecting with people.

Behind the scenes 🎥 building our dream craft room at the @becraftsy office in Denver.

A video posted by Official Craftsy Account (@becraftsy) on

And having a “hodgepodge” of these spaces is a good work environment for you?

Yes, it is. The open floor plan is always an interesting conversation, but it is genuinely great from a collaboration standpoint. It’s easy overhear conversations that are interesting, or that you can potentially add value in, and you’re able to join those.

But sometimes you don’t necessarily want to hear what everyone is discussing, so we have an unspoken rule that if I have my headphones on, don’t bother me. It’s a good way to signal to the world: “I’m focused right now, leave me alone.” We also have spaces designated for phone calls, because no one on our engineering team or product team has a telephone at their desk. So if anyone has to take a call or do something that would be disruptive or annoying to their neighbor, there’s a space for that.

What about when you can’t focus, or you get stuck on an idea. Do you have a place that helps you get back on track?

Yes! At Craftsy, we have this really weird chair that is built into a ball, and no one can really see you when you’re sitting there. When I’m at the shared desk, I do have a great deal of people stopping by to ask me questions, so I end up getting interrupted quite a bit. But I can go hide in this chair, put my headphones in, and get focused in a way that I can’t really anywhere else.

What is the coolest technology you’re currently working with?

Right, so we’re almost entirely an Amazon Web Services Cloud-based infrastructure, and AWS is constantly building new and interesting things. So, specifically Lambda, which is essentially a serverless code execution framework, is really interesting.

We’ve also recently started working with content delivery, content distribution network, Fastly. They’re really changing the game in terms of the way an organization or team is able to instrument and tune a content delivery network. It’s some really disruptive stuff with really cool technology. It’s one of the few things I can sit around and geek out about without having a practical application to my daily life.

What are some trends in the startup world you’re particularly excited about?

The first thing that comes to mind is devops. When I joined Craftsy 5 years ago, it was 16 people in a garage-sized room. Now, we’ve scaled to well over 200 employees, so we’ve had to change our approach. Devops, and the essential of working together in collaboration between an ops team and a development team, is something that I’ve been really passionate about and able to build here at Craftsy in the last 5 years.

Another trend that I’m excited about is the increase of engineering teams running without blame or finger-pointing.  At Craftsy, we really promote this culture, and we actually have an award for spectacular failures, to really make sure the team understands that they are here to be smart and take risks--which is a really essential part of a startup. The worst thing you can have is smart people who are afraid to take chances because they don’t want to get in trouble. So, the more traditional way of running an engineering team is calling someone out in front of everyone, or even firing them, when a mistake is made. Basically, making it clear that those mistakes have consequences. Instead, at Craftsy, we’ve made it kind of a badge of honor because it says you tried--even though it didn’t work out, good for you for taking that risk. We’re really getting past the culture of blame which is massively meaningful for a company that’s trying to grow.

Have you been at a company with this “culture of blame”? How did it affect your work?

Yes, and it wasn’t fun. The culture really affects the progress of the company and your own personal work. The culture of blame can discourage employees from taking risks, and keep them to doing as little as possible so that no light shines on them. I’ve also seen companies have so much process built up to protect itself from employees taking those risks, which means paperwork. You end up spending most of your day submitting ideas, and waiting for them to work through the various hierarchical systems of approval. At the end of the day, very little gets done. It’s mostly people reading, rejecting, and submitting different proposals and ideas.

That’s what draws me to startups, you get away from all that. Startups typically have either low process or paperwork, or none at all, allowing employees to innovate and take ownership. But, to really make the environment flourish, you have to get rid of the culture of blame in addition to the process and the paperwork. At Craftsy, we try to strike a balance. Just because we don’t have a culture of blame doesn’t mean people get a pass for bad behavior--there’s a difference between failing because you took a risk and failing because you didn’t do your homework. Mistakes due to lack of trying or lack of work are never okay. It’s not an absolution of responsibility. Rather, it’s recognizing that in the context of any business, especially a startup, you don’t know what’s going to happen, and you need the freedom to take risks and try different things.

What are some tips you can give people who are either working at startups or thinking about working at a startup?

Purely as an engineer, I would say not to believe any projection the business is giving you about growth. Rather than engineering a specific solution to meet a very assumed, quantifiable goal, engineer solutions that are simple and flexible. Reality will always surprise you, and at a startup it’s most important to be flexible and able to pivot when needed.

The business, the engineering team, the boss, everyone involved is going to think that have the best idea. But, there’s going to be plenty of times when lots of good thinking, lots of smart people, and lots of data suggested one course of action that didn’t produce the results you’d hoped for. That’s when you have to take a step back, stop what you’re doing, and change gears. It can be hard, it’s annoying to change course of action, and it can make people grumpy. You might’ve put a lot of effort into this particular idea and you don’t want to see it die even though it needs to. We all have to be deeply humble and leave our egos at the door and really let data and data analysis decide the path for us. When something isn’t working, channel Elsa and let it go.