Tech Leader Spotlight: Jason Waldrip


This week I had the opportunity to sit down with Denver tech leader Jason Waldrip. After I had him pick out a good beer for me (he brews his own, so I trusted his opinion), we got into the details of his career, experience with startups, the Denver community, and more. Continue reading to hear all about this local tech star. 

What are you currently doing in Denver? 

I am currently the VP of engineering at CommercialTribe. We offer sales training and employee development through a training platform to help people develop their skills in their careers. It's probably one of the first startups that I've worked for in a while that is addressing a problem that hasn't had a great solution available. 

The founder of CommercialTribe, Paul Ironside, has been a sales leader for over a decade, and has a lot of experience in coaching people. His vision solved for the unpredictable nature of the sales results by observing sales representative's behaviors and interactions throughout the entire sales process. That vision became CommercialTribe, which offers a platform where we can observe, assess, and coach individuals, and try to identify where they aren't adequately performing and what led to the loss of sale. 

For example, if you're hoping on the phone with a potential customer for a discovery call, the first part of the call is setting the agenda, which really lays the landscape for the entire call. If you don't conduct that properly, your potential customer may feel lost in the call which may lead to loss of sale or loss of the prospect. So we observe those situations in actual calls, recorded and practice scenarios on our platform. We then perform an assessment against a highly specialized framework where we use a mix of human and artificial intelligence to review those activities and interactions. Once we have assessed everything, we provide metrics to the company's sales manager, and give them guidance to coach their employees. 

You identify as a serial startup worker. What attracts you to startups? 

What attracts me to startups is the fast paced nature of things. When I worked for a healthcare startup, they were acquired by a large insurance company and I really notice how the development processes slowed and felt the corporate structure beginning. That's not a bad thing—some people thrive in those environments. 

In a startup culture, it's more about doing what you think is best for the company and asking for forgiveness when you do something wrong. In corporate culture, you ask for permission before you do anything which can delay productivity. So, for me, its a culture preference. I like the startup process better, and of course the ping-pong and beer helps. 

What's your involvement in the Denver tech community? 

I’ve spoken at a couple meetups about everything from Ruby to new languages like Crystal and React, kinda everything all over the board. I talked at Denver.rb, Develop Denver, participated in a few hack-a-thons, two of which I was awarded first and second place, so that’s been a really interesting experience. I’m also looking to host a hackathon to fill the void of the yearly hack-a-thons that used to happen a couple years ago. And then, of course, I attend as many meetups as I can.

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

We have an open office environment. Although I am VP, I like to be hands-on so I sit with the teams. I really like it from a collaboration standpoint, but not so much when someone gets sick. The face-to-face collaboration, sitting with someone, working the problem together—that’s really valuable. It also has all the typical startup perks: a kegerator, ping-pong, all that.

I would say that the open office environment is where I focus best. It’s really easy to go heads down and focus, and something I’ve done at a few companies now is have music playing all the time for everyone, that helps. When you’re in an open office environment, it can get noisy, but if everyone puts headphones on, you lose the collaboration aspect. So, if you put on music that generally everyone can share control of and enjoy, then people can take their headphones off and hear what’s going on while still be able to go heads down when needed.

What do you do when you get stuck?

Well, I work with a lot of smart people, and in the open office space it’s easy to ask. So, often I will just go to someone and ask if they’ve seen the problem before and how they addressed it. If I’m still stuck, I’ll go on stack overflow, those type of sites, to find the problem. If I can’t find it there, I work the problem to death until I solve it.

So, taking breaks doesn’t really work for you.

No. I have to keep going. I find myself not sleeping sometimes because I try to put my computer away, but if I’m in the middle of the problem I’ll be awake until 3AM thinking about it, working it in my head. So, for me, I just have to get it done.

Outside of work, what do you like working on for fun?

I really enjoy brewing my own beer. I started doing that about 4 years ago, and I really enjoy the science behind it. It’s somewhat like coding, you’re creating something, it’s problem solving and having that kind of ownership of a project that’s really rewarding for me.

I ski and snowboard, hangout with my son, the normal stuff. Ultimately, I’m a coder at heart. I love what I do and it’s ingrained in everything I do. I’m a problem solver and whatever it is I’ll try to figure it out and do it myself.

What's your favorite part about the Denver tech community? 

The wealth of talent we have in Denver. I've been all over the world, worked for startups everywhere, from Arizona, Philly, New York, Paris, and here, I’ve been everywhere. There’s a ton of talent here, and, I’d say San Fransisco better watch out because we’re coming for them. When you look at the actual startup scene here, the startups coming out of Denver are well known, take SendGrid and Ibotta for example—those are large, reputable companies. Even some of the older companies that started to create the Denver tech scene like and Ebags, those are Denver companies as well. There’s a very strong startup community that we built here and it’s impressive. Then you add TechStars, Turing, Galvanize and all these boot camps that the rest of the country is trying to replicate, all of which have roots stemming from the Denver tech community.

What’s the biggest difference between international tech communities and here?

Culture. I would say that, in general, Americans live to work while the rest of the world works to live. We take a lot of pride in what we do, and that’s not a bad thing. Now, Colorado has a work hard, play hard culture, and it’s different. But living in France, the team worked hard, but they would also take a two and a half hour lunch everyday, and leave at 5:30 to get drinks with each other. There’s a lot of startups that talk about that “family culture,” and you get that a lot more overseas. They’re more tight knit and spend time outside of work together. So, that was a pretty interesting experience that resonated with me and gave me some values to bring back into the workplace.

What values have you brought back? 

One of the biggest things I picked up while working in France is that everyone looks out for each other. And, it's not just a company culture thing, it's part of the country's culture. One regulation in particular blew me away, which is a law that basically states that if you're working for a company, after an initial 90 day probation period the company cannot fire you and you cannot quit the company, without getting or giving 90 days notice. Both sides are equally accountable. So, if I’m going to leave your company and work for another startup, I’ve got to give the company ample time to find a replacement. Vice-versa, if you’re going to let me go, I’ve got ample time to find another job. It’s really interesting and what it brings to the culture is employees that are really invested in the place they work. I haven’t had the ability to put something like that into place, but what I have done is brought some of those principles back. So, any employee that leaves my team, whether it be due to the performance of the individual or the company, I take at least a day of my time to sit with them and reach out to my contacts and help them find their next step. This is a small world, and you never know when you’ll work with someone again, so treating people with the respect they deserve is very important.

What's something you would improve about the Denver tech community? 

That’s a hard one, because we have a great tech community. If it was 5 years ago, I would’ve said more conferences in Denver, but now we have a good amount coming through and even starting here.

One thing I would say, and this is throughout the tech community in Denver and worldwide, is more apprenticeship and mentoring as a part of the workplace culture. Bootcamps like Turing and Galvanize do a great job at giving their students enough information to get out there and get a job, and we certainly hire these junior developers—but we sometimes throw them into the deep end. If they sink, we can hire a new one. There isn’t much opportunity to bring someone into the organization and develop their skills. We have to ask ourselves how we can help them reach that next level.

What are some up and coming tech trends that you're most excited about? 

I’m really into the world of decentralized applications and blockchain technologies, similar to what’s going on with cryptocurrencies, but moreso the idea of decentralized systems.

Look at what’s happening with net neutrality. When you have centrally controlled things that can censor and break trust, it’s really interesting to have a decentralized system where trust is built through the network and through the democracy of everything rather through the central authority. That’s really exciting to me, working off of rapid development processes, so every place that I’ve worked, I’ve introduced continuous integration, which is continuous deployment systems that allow teams to go from a release time of weeks to hours. So at CommercialTribe,  we’re able to release anytime we want, we push productions a couple times a day. It’s really awesome to receive feedback from clients at that pace. Additionally, I love new languages. React is huge. I love React. It’s definitely up and coming, and the entire industry seems to be moving to React. I’ve been programming it for a couple of years and really enjoyed the experience.

I’m also an advocate for a couple of cutting edge languages that are starting to make some way, such as Crystal. I’ve done a couple of talks and went to the first Crystal conference, where I was one of 22 people there in San Francisco. It was really impressive, people flew around from all over the world.

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