From Startups to Giants

Assumptions joining a giant company and what I’ve learned after one year


I was recently interviewing a product design candidate at Wayfair who reminded me of myself a year ago. He had spent years at startups. He had learned A TON about designing products. He was excited about the opportunity to work at a large company, but he was apprehensive. He worried about slow speeds and clunky design process. He worried about being challenged and becoming just another designer in a room full of them. He had a lot of assumptions about how big companies do design.

I’ve been designing websites and apps for the past ten years. And prior to this year I had only ever worked at startups and small companies. Joining a large company like Wayfair was the best decision I have ever made in my career.

There are countless articles all over the web about the benefits of spending time working for a large company. Google the topic and you’ll find Entrepreneur, Fast Company, Forbes, all talking about it. Then Google “The benefits of working at a startup” and you’ll find even more articles. So when you find yourself questioning your next career move like I was, what do you do?

The Speed

I assumed that giants “moved slowly”. When I joined Wayfair I remember asking “How fast do you move?” It was a leading question, I already thought I knew the answer and wanted the interviewer to lie to me and say “We move really fast!” My assumption was that large companies move like turtles compared to startups. But I was wrong in comparing the two. Startups don’t move fast and big companies don’t move slow. They move at whatever speed the leadership is capable of operating at. A big company with the right talent, resources, and customers, can ideate, build, test, QA and launch something at the same speed if not quicker than a startup with those same things. The question shouldn’t have been “How fast do you move?” It should have been “Tell me about the people on the team?”

Every Entrepreneur…

The Design Process

I assumed that big companies design with a strict process in place. I’ve learned that “design process” at large companies is often as chaotic as at a small startup. Prior to joining Wayfair I flew out to Facebook in Menlo Park, California, and during my interview said something to the effect of “I would expect that you guys have a rock-solid design process”… They laughed at me. I had made a massive assumption that large successful public companies like Facebook, Google, and Wayfair MUST have amazing design processes in place. This simply isn’t the case. Every company and every team within that company handles the process of designing products in slightly different ways. There is no textbook, and it’s often tumultuous. If it were textbook, it would be easy.

Being Challenged

I assumed that Wayfair had figured out most of the important things. Hell, they were a massive public tech company. Sure I’d add value but it would be iterative, and not super tough right? Wrong. When you’re a multi-billion dollar company with millions of customers, you are constantly evolving. You are constantly fighting to acquire the best talent, and keep up with technology. Because of this, the problems you tackle are tough. The new concepts you are generating are massively complicated. In order to keep this ship afloat everything we do needs to be top notch. And because of this, we place a massive amount of pressure on ourselves. We challenge our teammates and we challenge our designs. This is the second most challenging role I’ve ever held. ( I was in the Marines… )

( Not me, or is it? )

Becoming a Number

It took me a few weeks, but I eventually learned everyone’s names. One might assume that its easy to get lost in a large company and just become a number. But where there are more people, there are more opportunities to learn. I underestimated how much I would learn from my peers. I’ve learned that I’m not as good as I thought I was. Don’t get me wrong, I believe I am good at what I do. I pride myself on the quality of my work and the speed I operate at. But when I step back and look at all of the talented designers around me, I can almost always find someone who is better than me. There are better researchers, synthesizers, copywriters, block-framers, prototypers, engineers, orators, managers, visual designers, you name it. There are better people everywhere… And why is that a good thing? Because I can spend my time working with them and learning from them. Don’t worry about numbers, the more people there are, the more opportunities you have to grow as a designer.

This could be you and your other designer friends…


Experiencing design at companies of varying size is important in your early design career. If you’re at a big company, go try out a startup at some point (a topic for another post). And if you’ve only ever experienced startups, you NEED to spend some time at a large company. Your early design career should not be focused around chasing money. Take the pay cuts when you need to, in order to get the right experiences under your belt.

My brother recently pointed me to a Jeff Bezos “Letter To Shareholders” where Jeff talks about how there are two types of decisions. To quote him: “Never use a one-size-fits-all decision-making process. Many decisions are reversible, two-way doors.” If you’re considering trying out design at a big company, that decision is a two-way door. You can always go back to a small company. Opt for a new design experience, and don’t assume too much.

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