Why I’m Joining Square

Choosing the next step in your career can be hard. There’s plenty of advice out there, but every person’s situation is unique and there is still little guidance for Product Managers.

Hopefully going through my thought process in more detail will help those planning their next step or reconsidering their current one. I know I’ve benefited from hearing the stories of others. So consider this a very small way of paying it forward.

When discussing work, people (especially in tech) will inevitably mention work-life balance. The word “balance” opens an interesting discussion of its own. It pits the words “work” and “life” against each other. Instead of trading work for life, we should seek work that enhances life—for ourselves and others.

Three things came to mind when I thought about what this meant for me: staying uncomfortable, honing skills, and creating magic. These are meaningless quips without context, so read on for a few stories that might help.

Staying uncomfortable

A mentor from San Francisco once told me to continually push myself to remain uncomfortable.

If you’re comfortable, you’re complacent.

In the beginning of my career, “startup” and “uncomfortable” were synonymous. The thrill each day possessed kept you on edge. Wondering whether you would make payroll. Wondering whether your biggest client would churn. Wondering whether that next round would close. Wondering whether that key hire would join. It was taxing.

Then I realized the difference between uncertainty and discomfort.

Values available via crunchbase.com

My career started with uncertainty and discomfort. Diabeats was just a friend and me. I was the first hire at LaunchPad Central. And I was employee #100 at Grovo.

Joining another chaotic startup may seem like the obvious way to stay uncomfortable, with uncertainty at every corner, that is where I’ve spent my entire career. That is what makes me comfortable.

Meanwhile, larger companies are notorious for being slow, for having too much process, and for crippling innovation. It’s the unknowns that come with joining a public company that make me most uncomfortable. And that is what has me excited. I want to see if I can continue operating at a similar velocity and effectiveness in more complex environments.

Honing skills

I previously wrote about being self-aware and which parts of the design stack I felt I understood best. While I’m an [materials science] engineer by training, it was the world of design that sparked my interest in startups and tech. And it is design that I believe will play a differentiating role in the next wave of data interfaces.

Finding a customer-centric company with top tier design talent was critical. There are plenty of companies with incredible design, but aligning that with a worthy mission narrows the field quite a bit.

The Square NYC office was literally born from a design studio. Meeting with some of the designers during my hunt allowed me to see what design meant to the company at an individual level (no fluffy pitches). Interviewing with some of the design and engineering leaders sealed the deal for me. Not only were they experts in their craft, but they knew the bounds of it and how to wield it in unknown territory. Jack Dorsey sums it up rather nicely in the Golden Gate Bridge speech he gave at Square.

“Design is not just visual, design is efficiency. Design is making something simple. Design is epic. Design is making it easy for a user to get from point A to point B.
Engineering is design. Every engineer in this room, every operator in this room, every customer service agent in this room, is a designer. Because you’re designing constantly the interaction that you have with your tools or with your users or with your customers, and you’re trying to bring efficiency and take all the thinking out of that process.
So, everything we do here is design.”

I had found my chance to extend my ability to leverage the design stack.

Creating magic

Back in 2011, I had just moved to the Bay Area. I finally reached the promised land, the startup mecca. The promise of impact and innovation was around every corner.

I had a meeting in SoMa, but arrived early. With time to kill, I decided to go to a nearby cafe I visited a few weeks prior (I ordered an Americano, which will become relevant). As I approached the storefront, I reached into my pocket and realized I forgot my wallet—damn. Did I have to go all the way back home? Then I remembered that Square had just launched Square Wallet. Guess it was time to give it a try. ¯\_(ツ)_/¯

Walking into the cafe, I was filled with skepticism, fearful I would be laughed out as a patron without money. As I approached the register, the barista looked down, looked up, and greeted me.

Morning, Kevin! Another Americano for you today?

Uhh…what just happened? How did she know my name? How did she know my order? I never met her before. I just walked in. Attempting to hide my awestruck feeling, I quickly responded with a ‘yes’. She kindly brewed my drink, handed it to me, and said farewell. Without retrieving anything from my pocket—not my wallet, not my phone—I slowly walked out of the cafe and enjoyed my Americano.

The best technologies, they disappear, they fade into the background and they’re relevant when you want to use them, and they get out of the way when you don’t.

That is one of my favorite quotes about tech (which also happens to be from Jack Dorsey). The Golden Gate Bridge transports millions of people, and no one realizes how much work went into it, or that they’re even “using” it. That’s magical. I was able to purchase a coffee by simply walking into a cafe. That’s magical.

Unfortunately, Square Wallet was pulled from app stores in 2014. It might have been a failure, but I know what I experienced. It might have been too early for the market, but I believe in the future it paints.

Payments and commerce are a core piece of our lives. They are threads that weave through every day, often invisible narratives of who we are, what we do, and what we like. From the days of being trade-based civilizations to the more capitalistic ones today, commerce has defined much of how we live. That sure sounds like impact to me.

So I don’t know about you, but I want to build something magical. And that is why I am joining Square as a Product Manager.

The criteria I chose aren’t unique to my context. The rationale within them certainly are (e.g. big companies make me uncomfortable), but they should provide useful guard rails for you. Here are a few parting questions to ask yourself next time you find yourself with your shields down.

  1. Staying uncomfortable: What have you not done? What have others done that you admire? What would you regret not having tried in five years? Is this really a new dish or just scrambled eggs with sriracha? Do something that would surprise your friends and family.
  2. Honing skills: What is your superpower? What can you do better than anyone else? What complements that superpower? What holds you back from taking it to the next level? What topic do you avoid in interviews?Don’t be afraid to expose your weaknesses. Sometimes saying you aren’t good enough is the only way to get better.
  3. Creating magic: What problems in the world are important to you? What problems aren’t being solved well enough? What industries will have a rippling impact in the next decade? Have you been impacted by a particular product, service, or company? Don’t settle.

If you need a sounding board, or want to hear more details about anything in this story, let me know in the comments or on Twitter.

Do you have your own story to tell? I’d love to hear it! There is so much value in sharing our experiences, and I hope that mine can contribute a smidgen to the community.

A big thank you to Nikolas Laufer-Edel for reading drafts of this for me. He has a great story to tell on his journey to Lyft. I hope he writes about it one day :)