I left big tech ~9 months ago to join a series A startup and since then I’ve learned a TON about the startup ecosystem. This is the email I wish I had read when I was considering moving to a startup.
If you’ve only worked in / considered big tech, you have to understand that things in the startup world are very different. A few major notes:
EVERYTHING (comp, interviews, the job itself) is less standardized. Companies are run by people who basically do whatever they want and work however they want. Things also very VASTLY depending on the stage of the company. A first or 2nd hire at a preseed company is much different from a series D+ hire (basically the higher the letter in the series, the bigger the company).
Networking and reputation are more important. A bad hire is very costly for a startup (your company might only have 12-18 months of money left), so they tend to put more effort into avoid this. This means having good references and being someone desirable to work with are more important.
Upside and downside are both much larger. Engineers who got into Anthropic or OpenAI early are now worth 100M+. Engineers at COUNTLESS other companies got paid 150K + 200K in equity over 4 years only to have that company go bankrupt and their equity go to 0 value. The second person (and frankly most people) would have been MUCH better off in big tech.
I have more general notes which I may write about another day, but let’s focus back in on the interview process and to get a job at one of these companies, starting with the application.
You can find jobs at startups on LinkedIn or anywhere else you normally do, but I prefer to look in more curated places:
1. YC keeps a list of their companies and jobs they have open: https://www.ycombinator.com/jobs
2. a16z build published jobs frequently in their newsletter: https://a16zbuild.substack.com/
3. Startups gallery has good filtering and jobs listed:
https://startups.gallery/
Those are just a couple examples, but you get the idea. There are dedicated places where you can find these jobs listed and apply just like your would to a big tech company.
Now I personally would NEVER cold apply to a startup job. Startups, particularly super early stage ones function more like a friend group than a company. Everyone works together super closely, you often don’t have a ton of time for other friends, and everyone has ownership in the company and is deeply invested in the outcome.
This makes referrals and a warm introduction 10x more powerful than the same in big tech. Instead of getting a hiring manager intro and having to go through the same loop, you can get a direct intro to the CEO, and get invited to an onsite interview or work trial after just a preliminary chat.
If you are like me ~1 year ago, you might not know ANYONE in the startup space, and think it’s impossible to get a referral like this. It’s actually much easier than you think.
Here are a couple things you can do (these all work best if you live in a startup friendly city, ie SF or NYC)
1. Go to networking events, dinners, conferences, etc and make it known what you do. This lets you open a conversation and people looking to hire for your role will automatically start interviewing you.
2. Build in public / have proof of excellence. This could be a paper you’ve published, a social media presence, a product you’ve built with a few users, etc. If you goal is a startup job, really focus on X (formerly twitter). Both founders and investors have chosen this as their primary platform. YOU DO NOT need a huge following to get their attention. X is very good at surfacing content to hyper-niche groups of people. Build you profile out and start sending DMs to founders building stuff you feel you could contribute to. A founder literally DMed me WHILE I WAS WRITING this email from my very minimal X profile.
3. Join niche communities in your space. There are online communities for most industries, both free and paid. I built a discord community into my website The Daily Dev so you can learn System Design, and network with me and your peers. We now have current and aspiring engineers from all sorts of companies, you can pick each others brains, demonstrate your expertise, build relationships, and get referrals & warm intros.
OK so now you’ve either gotten a warm intro, a dm from a recruiter or a response to a cold application, what does the actual interview loop look like?
This is almost impossible to predict, but I’ll give you the rough guideline
1. A chat with the CEO / CTO. Whoever is leading the engineering function will want to speak with you at some point. Some companies have this as the first step, some as the last. This is close to a behavioral round in big tech. They’ll want to know why you want to work at this company (have a good answer) what you bring to the table, and they might ask you some classic questions like describe a time you did [insert something here].
2. A technical assessment of some kind. This could be leetcode style but it is much less likely than in big tech where it is almost certain. You could be asked to design and implement a small feature, explain how you’d solve a problem they’ve recently faced, or how you’d work with a specific technology they use. For example if you were interviewing for a Twitch competitor, you could expect some questions related to video live streaming.
3. A take home project. This is not guaranteed, but more and more companies are rolling these out to see how you work on real projects. For these, go ahead and use AI and work as you normally would, but MAKE SURE YOU CAN EXPLAIN YOUR WORK. If I ask you to build a simple website that tracks every pixel a user clicks on, I want to know what tech stack you picked, why you picked it, how often you send updates, why that’s the right amount, etc. You don’t have to do it perfectly, but make sure you can EXPLAIN why you did what you did.
4. A work trial. These are becoming more and more common, especially at early stage companies. This could be 1-2 days or a full week depending on your and their availability. Obviously do your best work, but also make sure you figure out if the company & culture is something you’re interested in.
Hopefully this was helpful.
Arjay
P.S. If you’re looking for a community where you can network with your peers, meet people learning the same thing as you, get feedback on your startup / personal projects and chat all things system design, you’ll love The Daily Dev.