I'm a big believer that when you close any meaningful chapter, it's a worthwhile exercise to sit down and reflect on the most valuable things you learned from the experience. I've done this before when I moved on from working as a full-time data scientist at Squarespace.
Now the time has come to do the same for Hugo, my first full-time role at an early-stage startup. This isn't a complete list by any means, but these are some of the most valuable lessons I learned:
Growth Spans Domains
When I joined Hugo, I was initially spending most of my time on the marketing side of the fence. Over time I began to gravitate closer towards product. When it was time for my tour of duty to come to a close, I was touching parts of the entire funnel. I got my hands dirty with tactics and concepts that I never thought I would, and I learned a ton doing it.
Our growth team was cross-functional, so every week I was hearing about developments on social, marketing, product, design, engineering, and customer success. I can't overstate the number of times that I had to pause during a call and think, "Hey, I didn't know it worked like that." Looking back, these moments were challenging, but invaluable.
Product Iteration Wins
I was consistently impressed by the speed of iteration and rate of shipping at Hugo. We would ship meaningful product improvements often once, sometimes even twice a week. Not only did this impress customers, but it gave me a sense of momentum in my work. I didn't realize before how motivating it is to watch the product you're working on evolve into something incrementally better and better each week.
Empower Others to Act
This is somewhat of a prerequisite at a startup with <30 employees but I still think it's well worth calling out. It's easy to say you do this well, but in reality there are lots of things you have to get right.
There needs to be a certain level of transparency so that team members have enough context to make decisions. You need a suite of tools that enable ICs to 'do things' without leaning on others too heavily. Finally, you must communicate strategy well across the org so that everyone is moving in the right direction. Once you have all these pieces in place, then speed and autonomy can follow.
Asynchronous Collaboration Works
Teams all over the world have been increasingly figuring this one out over the past year. It took a bit for me to get used to this working style, but once I did, our team culture of writing everything down and making it available, deferring to looms rather than 'quick chats,' grew on me quickly to the point where now it's hard for me to imagine going back.
What It Takes to be a Founder
I've held the view for a while that at some point in my career, I want to start a company and build something meaningful. After working at Hugo for the last 1.5 years, I'm still convinced I want to go on that journey, but I'm much more informed on what being a great founder entails.
Read all the tweetstorms and blog posts you want, they'll tell you that it's hard. It's harder. The amount that is put on your plate and the responsibility that you take on honestly is pretty intimidating. Not to mention the ups and downs of a multi-year emotional roller coaster. I still want to be a founder one day, but now I feel like I know what I'm getting into, and I'm better prepared for that moment. Thanks, Josh and Darren.
I could go on and on but I'll stick to the points above as the ones that stand out the most upon reflection. I'm excited to watch from afar as Hugo continues to grow and spread throughout the working world. As for my next move, stay tuned for another short blog post with more details. Until next time.
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