How This Missouri-Native Broke Into the DC Tech Scene

Andrew Gassen

July 24, 2020

Andrew is literally writing the book on building effective teams in tech. He's also teaching and building with no-code tools, all while working a full-time job at VMware.

Hi Andrew! Can you give us a short intro to who you are and what are you currently working on?

Sure! I’m Andrew Gassen, a Missouri-native that moved to Northern Virginia in 2015 when the startup I was working at shut down. I took a product management role at Pivotal Labs (recently acquired by VMware) and moved my wife and dogs from steamy Orlando to the DMV region.

I’m currently a Customer Success Director at VMware. I work with large organizations, primarily Fortune 500 companies and government agencies, and help them make the transformation into modern software organizations. There’s a lot of process, politics, tooling, and software involved, but at the end of the day, the key part of my day-to-day job is building relationships and understanding people. After all, it’s the people that ultimately move an organization from Point A to Point B, wherever that may be.

“If I think my product is not a fit for you, I will tell you. If I think you’re making a bad choice, I will tell you. If I screwed up, I will tell you.”

When it comes to side projects, I have a nasty habit of stopping things once I’ve figured out the tough bits. One area where I don’t stop, however, is education. I teach sessions at a couple of local startup accelerators, do one-on-one coaching with non-technical founders, and am currently building (very slowly) an online course. My primary nights and weekend focus, however, is on completing a book I’m writing on how to build and operate high-performing software teams.

What's your backstory and when did you realize you wanted to work in tech or startups?

I actually made it into the tech world by way of the video game industry. For as long as I could remember, I wanted to make video games. I have binders of scribbles and notes and drawings from my childhood, but growing up in a small farm town in Missouri, I had no idea how to get started actually making a video game. 

When I finished my Bachelor’s Degree in Business Administration, I didn’t like the career options available to me so I decided to go to graduate school. On a whim, I applied to the University of Central Florida and its FIEA (Florida Interactive Entertainment Academy) program. I got it!

I graduated FIEA and took a job at EA Sports. Contrary to what many people would think, EA was actually a great place to work. I just didn’t like being a small piece in a larger machine. My professors from FIEA had a small startup working on education technology. They heard about my lack of enthusiasm, and they offered me a job to run product management at this startup.

I had no idea what I was doing, but that’s okay! I learned, and it was great. From that point, I knew the tech industry is where I wanted to be and where I could add the most value to the world.

What are the tools of your trade?

This is an interesting question for me to think about. My brain immediately tries to create “buckets” to answer this, so rather than fight that mental model, I’ll roll with it.

Workflow Tools - Software packages that I use to do my job.

  • Trello for shared team tasks
  • Miro for digital whiteboarding
  • Slack for communication
  • GSuite for spreadsheets, slideshows, and word processing
  • Gmail for customer interaction
  • OneNote for personal note-taking (iPad version)
  • LinkedIn for networking and research

Human Tools - Skills or personality traits that help me succeed at my job.

  • Curiosity - There’s always more to learn. My mantra: Future Me will never know as little as I do right now!
  • A focus on customer outcomes instead of product adoption or consumption
  • Sustainability - I don’t work crazy hours, so I must be effective about planning my time and priorities
  • Real Relationships - The folks I work with aren’t “clients,” they’re people. I take the time to build actual relationships, know what makes them tick outside of work, and establish a level of trust that makes me the first phone call
  • Humor - Most people in the workforce are children pretending to be grown-ups. Sometimes humor takes the edge off and allows people to be their true selves.
  • Honesty - If I think my product is not a fit for you, I will tell you. If I think you’re making a bad choice, I will tell you. If I screwed up, I will tell you.

Side-Project Tools - Software I’m using in my side projects!

  • Bubble.io - I can’t code, so Bubble is how I build web applications.
  • Adalo - In this bullet, I still can’t code. Adalo is how I build mobile applications.
  • Figma - UI designs and vector creation
  • Canva - Social media banners and similar art
  • Podia - My online storefront for books and such
  • Substack - My Team Signal newsletter
  • Wordpress - My personal blog

What have been the most helpful or influential resources you’ve learned from?

This is a tough question for me to answer, specifically because continuous education is a key part of my day-to-day life. As I write this, the bookshelf to the left of me has 50 books, my Nook account has another 18, my Kindle account has too many to count, and I listened to 18 books on Audible last year while commuting for work. 

I’ll read about anything, but I think it’s important to note that I’m not looking for answers or a specific approach to anything. I certainly value other experiences and insights, but it’s unfair to expect something to work in my scenario simply because it worked for someone else. I’m looking for lessons and abstractions, not scripts and playbooks.

“Building and operating high-performing software teams is hard, so I’d like to make it easier.”

That being said, I’m a big fan of the books put out by the folks at Strategyzer and Sense & Respond Press. The team at Basecamp has a unique view of the world that I appreciate, but honestly, a lot of what I’ve learned has come from on-the-job experience. I’ve made many, many mistakes. So have my colleagues. Fortunately, the culture at VMware encourages us to learn, improve, and share our lessons broadly.

As far as specific authors, I like some of the stuff put out by Paul Jarvis, Rob Walling, Josh Seiden, Eric Ries, Charles Duhigg, Ben Horowitz, Dan Olsen, and Marty Cagan. There are countless others I could list, but those come to the top of my mind. 

I read The Daily Stoic by Ryan Holiday as part of my daily ritual, am currently finishing up Superfans by Pat Flynn, and am listening to What You Do Is Who You Are by Ben Horowitz when I travel.

How did you get the job you currently have? Or, if you’re working on your own project/business, how did you come up with the idea and get it started?

I’m actually on my second stint at Pivotal/VMware. The first time I worked here, I applied to Underdog.io and used their service. It was an incredible experience! The initial opening was for a role in New York City, but once I was connected with the Pivotal recruiter, we decided the DC opportunity was a better fit for both the company and my family.

After 2 years in a manager role, I left Pivotal. I wanted to see if I could take my knowledge and experience and apply them to a startup, so I went to a cool company building voice apps (Alexa, Google Assistant, Bixby, etc) called XAPPmedia. I’ll be the first to admit my failures in this role. The struggles I had bringing new principles to the organization really helped pave the way for my growth and successes in my current role. After a year at XAPPmedia, I had an opportunity to come back to Pivotal in a sales-ish role. I’ve been doing this for about a year and a half and love it!

As far as my side project goes, I decided to focus on “software teams” because of what I’ve seen happen at organizations across the globe. There’s a big focus on “agile” at the practitioner level and “digital transformation” at the executive level, but the fundamental people part is underserved in my experience. Building and operating high-performing software teams is hard, so I’d like to make it easier.

What advice do you have for someone looking to break into tech? Or, what advice would you give yourself 5 years ago?

I think the best advice I could give boils down to two things:

  • Don’t be a jerk
  • Be radically helpful

The first point is about how you carry yourself, how you share what you know, and how you treat others. To be quite blunt, many jobs out there aren’t much fun and the companies aren’t great to work for. As a job seeker, you can scoff at those opportunities or you can learn from them, possibly even make them better.

The second point is what I wish I would have known when I was younger. Heck, I wish I would’ve emphasized this more even a few months ago. There’s a universe of knowledge out there that I don’t know. Rather than focus on all the missing knowledge, how can I leverage what I DO know to help others? 

Was there anyone in particular you want to shout out who helped your career along? An individual, or community?

There’s a very long list here, but I’ll try to be concise! Erik Sand was a coworker of mine at the first startup I worked at. Just about every skill I have related to interpersonal relationships comes from him. I definitely wouldn’t be where I am without Erik!

Caroline Hane-Weijman was my manager at VMware and really pushed me to embrace all the different aspects of my personality, then leverage those traits to deliver value to the world. She essentially gave me permission to be who I am.

Sibyl Edwards and the entire BlackFemaleFounder community in DC welcomed me with open arms from the day they formed. I grew up in a town that was overwhelmingly white. The things I’ve taught and shared could never amount to what I’ve learned about the importance of diversity and inclusion from this group.

Finally, the most important of all: my wife! She was born and raised in Central Florida, so when I suggested we move to the DC area to pursue this tech job, she could’ve said no. Instead, she believed in me and my potential and hopped on board. Now we both work at VMware, have an amazing friend group, and love living in this part of the world. Without her faith in me, who knows where we’d be.

Where can we go to learn more about you and your work?

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