Two months of life at a startup

After deciding to leave big tech, I wanted to join a startup because I wanted to ~learn~. I’m pleasantly shocked at how much learning I’m doing every day.

I’ve had to learn stuff at previous jobs but it was almost always limited to learning a new technology (Heroku, Kubernetes, Borg, whatever). At my current job, the technology isn’t monstrously complicated but startup PM-ing is a whole different beast. People say it all the time, but it doesn’t hit until you’re in it.

The biggest change for me has been how close I am to every single function. It’s exactly this proximity that allows me to also see “dysfunction” (and to be clear, this is ok and normal!)

When you’re at a large company, the gaps in your product are either invisible or filled by people or processes. When you’re at a small company, the skeletons don’t stay in the closet; gaps in your product become glaringly obvious. For instance: sales teams can and will tell you about inconsistencies in your roadmap, documentation teams will not document things you as a PM don’t document, you have to figure out how to price your own features (COGS for software is…not fun?), customers will call you out if your API and CLI can’t do what your UI can do and vice versa, the list goes on.

These issues exist at larger companies too but are diluted by the time they reach the product team. Adjacent teams often build their own solutions on top of the product as bandaids or companies hire more people (solutions architects or customer support reps) to solve the problem instead of fixing the root cause in the product. Big companies can easily get away with it because a) they have the resources to do so, and b) their default mode is to exist, not to die. Startups don’t have the luxury.

Back to my original point, I’m learning a ton about other functions (especially ops, sales, solutions, marketing) and how they work. I see how product decisions directly affect partner teams and customers. The feedback loop is so tight; it’s making me a lot better at my job. This is why it’s so hard to create innovation centers or startup-vibes at larger companies. You can simulate it, but it doesn’t ever come close to the real thing.

This experience is also teaching me to prioritize better. I’m action-oriented to a fault and when I see a problem, my immediate urge is to fix it. But a startup is full of problems waiting to be solved and I would be underwater if I tried to do everything. Learning to say no (usually to myself) is new to me and I’m learning as I go.

I’ve also come to recognize that it’s only when you are surrounded by an A-team that startup tribulations translate to learning. Otherwise, it’s just regular chaos.

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