My Experience Working at a Software Startup

September 19th, 2019

From May until September, 2019, I was working at a software startup, Resource. Ever since first hearing Joe Gebbia's story about Airbnb while I was at RISD, I've been fascinated by the story of going out to California (where I was born) and working with a team starting something from nothing. I actually was lucky enough to meet Gebbia while at RISD for an event at the career center. I filled my entire slot babbling incoherently, and then at the end he was like "Cool." ~ facepalm ~. In May of this year, I decided to take a wild bet and join a group of ten-ish (now 14) people who are on a mission to redesign the recruiting process to be something more equal, and even fun. Having found most recruiting processes to be deeply dehumanizing, and boring, I was pretty interested.

In their own recruiting process, Resource ran things in a way that made me feel they knew what they were talking about. Every email was filled with thoughtful takeaways and emojis that made it clear a person wrote the email. After all my interviews, they asked for my feedback on how I thought they did. Once they extended an offer, they opened up references of people who no longer worked at the company. I felt like it was obvious that this was the future of how everyone would run their recruiting function, so I signed the paperwork and packed my bags with Emily's blessing. As a part of the deal, I agreed to adopt a dog.

Over the past few weeks I've had a few distinct learnings that I wanted to share, to give others a sense of what my time here has been like.

Innovation is chunky. Sometimes when I was working on something weird / new, I'd spend my time reading a book, or creating some ugly drawings. After a week, it might not look like a huge breakthrough had happened, but that's just the nature of the beast. In the words of my teammate Troy, it's "drudgery, drudgery, drudgery, breakthrough. Repeat. This experience has helped me feel more comfortable with ambiguity

The Design Process is Transferrable. As a new grad, I felt a lot of (justified) pressure to specialize. The way I interpreted pressure was that "being good at one type of design doesn't make you good at another type of design". I think there's a lot of truth to that statement. I really don't think I could do a good job designing a font if I tried. I would design a terrible house. Shoes baffle me. However! In the past year I've worked as a toy designer, branding designer, ux designer, and installation designer. As far as I know I've managed to do a good job at all of those. "Good" meaning my clients seemed to be happy with the work I created for them.

Coaches can be amazing. At Resource I had the privilege to work with two people who come from coaching backgrounds, and I found them to be amazing collaborators. Now that I have these experience, I often find myself asking "how can I be more of a coach for this person?" when I'm supporting someone.

Being a solo-designer improves your presentation skills I had a lot of critiques that ended on ambiguous notes. I was used to relying on coworkers to explain in designer-terms what about a design wasn't working, and being able to easily assess if a design process issue was at play. As a solo designer, it doesn't make sense to require the head of sales to brush up on design process. They should spend their time making sales calls! That forced me to be able to communicate my ideas simply. "If you can't explain something to a five year old, you don't really understand it" comes to mind. Of course this slows things down, because there's an extra step in honing the communication, but now that I'm working on a design team with other designers again, I see how much more smoothly my reviews are going now that I had that practice. No more "Feels kinda wonky right??" or at least not in a crit environment.

It might be a good idea to tell your boss you're thinking of leaving before you make any decisions. I'd like to pretend that all my lessons are from trying things / taking risks and then awesomeness unfolding. In reality, I made a pretty big mistake that I want to own and document so others can learn from it. In short, I interviewed for another job and accepted it (this happened over the course of ~2 weeks) and then resigned without speaking to anyone at this job before I made the decision.

The effect of this was that I blindsided my coworkers and my closest coworkers told me I had seriously damaged their ability to trust me in the future. This was a pretty big surprise to me, because at littleBits, people left with no notice all the time. I was told that this was "normal", and part of being "professional" was to just not be that affected by it and move on. In my first week or so at Resource, someone on the sales team left, and it was a complete surprise to me, which made me feel like it might be the case that things worked the same at Resource.

I think that neither party here is "right". Rather, my takeaway is that everyone has different expectations of what is safe or unsafe to talk about, and it's important to find those boundaries and not assume that it's the same from person to person. I believe that no one owes anyone else closure, and boundaries should be treated as facts (it helps no one to try to force someone to communicate about something they don't feel comfortable communicating with). That said, I believe that we should always try to find the most honest and authentic version of a relationship that both people in the relationship feel comfortable with.

A helpful example that my colleague Troy offered was that if the company was struggling financially, he would tell us, even if it meant it might temper our excitement and progress (thus hurting our ability to stay afloat). I think in my case, my trauma of being laid off at littleBits hampered my ability to place trust in others.

I know a lot of people will naturally resist this idea and want to say "Companies aren't people! you don't owe companies sh*t. Companies will fire you the moment you aren't useful to them" but this is an absolute statement, and absolute statements don't hold up to complexity (and life is complex!) In hindsight, my closest colleagues had done a lot to earn my trust, so I should have at least let him in the loop earlier that I was considering another option. I do still believe that it's not realistic for a company to claim "we won't hold it against you if you're considering leaving." Ultimately, someone is telling you that they aren't 100% "in it" and that's information that is relevant to the team dynamic and important to take into account. That said, it's always going to be scary to bring up something that you think will lead to pain. A quote comes to mind "Courage is knowing it might hurt, and doing it anyway. Stupidity is the same. And that is why life is hard." - Jeremy Goldberg.

Despite this causing some pain, I'm really grateful that my colleagues shared with me their honest feelings about how they were affected, because I think this has been a huge moment for me to learn and reflect on how my values show up in my relationships across my life, inside and outside of life.

This summer was one of the most rapid periods of growth in my life.