Reflecting on my first startup job: Part 1 - Surprises

15 August 2014

I just wrapped up my first job at a startup. Wow, was it an experience. The company I worked for hired me knowing that I had minimal (really, no) technical background, and offered to teach me how to code. After a few months of intensive, hands-on learning, I was working just like a developer. By the end of my time, 1 year and 9 months later, my role was a mix of product management and engineering.

Since I have a bit of time before starting my next chapter (business school), I wanted to reflect on my first job at a startup. This is to help me remember what has happened over the last couple of years, and to show others what startup life can be like.

To keep the posts as short as possible, this will be a four-part series:

  1. Surprises
  2. Regrets
  3. What I learned about the startup world
  4. What I'll look for in my next tech job

Before getting into surprises, I want to caveat that a lot of my experience was impacted by the kind and size of startup I worked for. Specifically, the company (which I'll keep anonymous here to hide it from Google, but which you can probably figure out by the description) is an aggregator of daily deals, like a Kayak for the Groupon and LivingSocial space. The company has raised a couple of rounds of VC funding, and is currently doing well. Throughout my time there, there were 20 - 25 employees, with some turnover; I was roughly employee #25, and not a manager of others. I was part of the product / engineering team, which accounted for a little more than half the company.

Part 1: Surprises

When I started out, I knew that the startup world would be radically different from the older, more hierarchical worlds of finance and corporate strategy where I had come from. Some of the biggest factors about my startup job which surprised me were:

Work at a startup can be fairly scientific

Our startup followed the "lean" startup philosophy (defined later in this series). This meant that even though we were building a new product (no precedent) and were basically the only player in our field (no competition), everything we did was rigorously scientific. We would come up with new ideas, build out prototypes, test the prototypes to collect quantitative feedback on user engagement and monetary performance, and make decisions based off of numbers. This was a lot more grounded and methodical than how I thought startups would be.

It wasn't a constant scramble

On TV (or perhaps it's just Silicon Valley), you see startups as a few people working in a room for long, long hours, scrambling to do a thousand things at once and putting out fires all the time. The startup I worked at was large enough where that wasn't true anymore - we all worked hard, yes, but we set short-term goals for ourselves on the scale of a couple weeks at a time. We didn't have to run around putting out fires (though that happened sometimes); we could instead plan out our days and weeks. With a bit of size (and the cushion of revenue), things become much steadier and feel like ... well, a normal company.

There are a lot of things you can't do by yourself

Another false impression from the media is that at a startup, you have people who are all jacks-of-many-trades. It might be the fabled "full-stack developer", or the BD-finance-ops-sales-marketing business guy. In reality, my startup was large enough where there was a fair degree of specialization. Not only would different engineers specialize on different parts of the tech stack, but you would have specialization on the business side as well. This is not to say that the company forced us to specialize in one specific area; rather, specialization kind of happens naturally as people work on projects that they find interesting. This led to a lot of teamwork involving different functions on our major projects. This style of working allowed us to learn from our peers, without being individually overwhelmed all the time with steep learning curves in new disciplines.

Big things can change much faster than you'd expect

Maybe it's not an overnight pivot, but even for a company of our size, fairly big changes could occur fairly quickly. Our core product wasn't going to change overnight - especially not when it's bringing in money. But a new product idea can sprout up from nothing and begin demanding resources in just a couple of weeks. Or, perhaps a new project management system is going to be put into place immediately, because somebody's already researched it and figured out what to try. There's a lot going on "behind the scenes" with everybody working on different things, so at times it can feel like change is coming from nowhere and taking effect surprisingly quickly. For better or worse, we as employees had to take all these changes in stride and adapt to the latest version of reality.

Even with numbers, you'll still spend a lot of time interpreting and storytelling

Our company was pretty good about relying on numbers whenever possible. But, as is true everywhere else in life, numbers still need to be interpreted, and storytelling is still a major factor in making decisions. A minority of split tests do extremely well or poorly. Most perform mediocrely, and you get a lot of numbers that don't always tell a clear story. In those cases, you still have to construct a plausible story and keep going, but there will always be a nagging feeling that perhaps there was a better interpretation or explanation for what happened.

You will feel the impact of cultural or morale shifts

On a team of 25, you get to know your coworkers pretty well. You may not work with all of them directly, but over the course of lunches, happy hours, and company events, you get a sense for who everyone is, how they work, and how they feel. In such a small environment, I was surprised both by how fluid our company's culture and morale were, and how much I could feel these intangible aspects shifting. Sometimes these changes were bad - when a person got fired, there was a palpable heavy silence in the office. But sometimes they were energizing - when a new, large product initiative was announced, everyone felt more perky and excited. Even if I was in no way involved with the precipitating change, every change reverberates throughout the company.

Coming up next in the series: regrets.

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