How To Get Hired At A Startup

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Sometime during the real doldrums of sophomore year of high school, my high school counselor sat us all down and whipped out a 72-page Powerpoint information that was, at the time, the most boring thing I had seen in my entire life. It was about how to get hired, and all of the advice was irrelevant for the kinds of people who would go on to work at startups.

This essay is going to be a less boring and more useful guide to getting hired at a startup. The advice may work outside of startup world, too — but we are going narrow to be as useful as possible.

We need to get a few disclaimers out of the way first, though:

• You should work on whatever you want

• Most startups suck

• Working at a startup is not your most likely path to becoming moderately wealthy

Here is a guide to getting a job at a startup.

What not to do

A lot of people who want to work at startups reach out via email or DMs saying they’ll do anything, or that they’d like to help however they can. That’s not very useful because then someone has to figure out what you should do, and that takes work. Those kinds of emails rarely get replies.

A lot of people also just find jobs on LinkedIn or other boards and then apply through official channels. This can sometimes work (especially in addition to the steps below) but it shouldn’t be your only way of reaching out to a company that you really want to work for.

The other big thing not to do is give up.

What you actually should do

> Find a company that seems to be hiring that you would want to work for.

Some lists:,

You could also browse websites like Crunchbase and find companies that raised recently. Or you could join a community like to find new opportunities.

It’s fine to reach out to companies without any jobs posted.

> Brainstorm ways you can be valuable.

For each company you plan on reaching out to, write a short memo about how you can be valuable to that company. The best way to show how you can be valuable, especially at startups, is to make it obvious that you can help them make more money. In almost every case, you will do this by helping a company 1) find new customers, 2) increase the amount of revenue they make per customer, 3) cut costs, or some combination of those options.

One example structure of a memo could be the following:

• Disclaimer that you don’t have enough context, but you’ll make some assumptions

• Your own summary of what the company does

• Your ideas about how you could help it increase revenue or cut costs, or both

If you’re amazing at making viral TikTok videos — a skill which may raise some eyebrows — then your memo could focus on the actual revenue impact that viral TikToks would have for the company. Remember that lots of people spend too much time talking about what they’re good at and too little time extrapolating to explain how that thing will help the company make more money. Focus your memo on the latter.

Note: You may not actually send this exact memo to the company, but it helps you organize your thoughts.

> Email the founder.*

There are so many theories about cold emails, but generally when you are emailing startup founders you want to ditch all the guru shit and just write something short and sweet that says how you could help.

Ex: Hey, Jordan - my name is Carter. Reaching out to suggest we work on some writing/content together.

I used to write for [X company], where I built [X thing] that drove [X outcome]. I’ve also written with [notable client] and [notable client].

Enjoy the stuff you have put out so far. Think there is a lot more we could write about (that could be valuable for [X] and [Y]) and would love to share ideas (here’s a link to a memo I put together for you).

Have 15m this week or next for a quick chat?


Your email could and probably should look way different, but the point is that it should be concise and explain how you help and why you are good at what you do. You can link the memo you wrote if you think it will be valuable. A few tips on getting the right email:

• The founder’s email will usually be You can also use tools like Nymeria to help you confirm.

• If you don’t want to send an email, try LinkedIn or Twitter (or send messages on all of them).

• If you want a warm intro, another approach is to email VCs who have invested in the company.

*If the company is large (post Series D or so) then depending on what kind of skill you want to offer, you could try reaching out to the relevant Director/Lead of the company for that department.

> Repeat this process with at least 50 companies.

The odds of someone replying to your email depend on a number of factors:

• If you are legit/have notable experience or achievements

• How well you wrote your cold email

• Whether the founder thinks they have a need for what you are offering

• Whether the company is able to hire or considering hiring at the moment

• If the founder even saw your email (things slip through the cracks)

• If the founder remembered to reply

You get the point. There are lots of reasons someone might not reply, which is why you should email a lot of companies you are interested in working for, not just one. If you send a couple emails and don’t get a reply, you could write off your failure to bad luck. If you send 50+ emails and do not get a reply, you know there is more likely a problem with something about the way you are pitching people on yourself.

> Wait, then follow up if people don’t respond.

Sometimes people don’t respond because they don’t want to, but often it’s because of one of the other reasons on the bullet point list above. Not following up is a serious mistake — you could be losing out on the job of your dreams simply because the founder didn’t see your first email.

Following up once or twice is good practice. Following up 3+ times feels desperate, and by that point it is usually clear that the person doesn’t want to respond. (Also, remember that you are not owed a response.)

> Respond very quickly when they get back to you.

Responding quickly impresses people. While you’re actively cold emailing people and hunting for work, keep your phone or laptop close (even on the weekends — many founders work weekends). Turn notifications on if it’s helpful. Once somebody responds, reply as quickly as you can.

No need to work out the game theory of response times in order to avoid looking too desperate — this isn’t Tinder. When you’re looking for a job, replying fast just makes you look good.

> Have a call with them.

When someone wants to chat with you (congrats) it’s important that you do a good job on the first call. A useful question you can get answered is this:

“What’s the most important thing you need to solve right now?”

A few other tips for the call:

• Take notes of the most important stuff and send over a follow-up after the call with the key learnings highlighted. Don’t take notes to the point where it’s inhibiting your ability to be present, though.

• Calls are scary. One way to practice is to write a memo answering a bunch of the questions you think they’ll ask you. You won’t read these off word-for-word on the call, but it’s useful to be prepared with thoughtful responses ahead of time.

Then there’s also the obvious stuff, like doing your research ahead of time and caring about details.

> Do the little things right.

Some little things you can do right:

• Don’t act desperate. It’s fine to follow up and even be a bit pushy, but don’t say things like “man, the job market is tough right now - I really want you to give me a shot”.

• Be grateful. After a call, a quick ‘Hey - appreciate you taking the time. It was great to chat’ is good. 

• Send emails proactively. Imagine the conversation didn’t go anywhere but 3 months later you see the company raised. Sending an email like ‘Hey - congrats on the raise’ can go a long way.

• Don’t bullshit.

• Be yourself. Sometimes people put on ultra-professional airs when they start talking about work. Don’t do that. Just be yourself. People will appreciate the authenticity. If they don’t, you shouldn't work with them.

> Don’t give up.

The above guide is less likely to work if you 1) don’t have many skills that are useful for startups, or 2) aren’t very good at the skills that you have. If this is the case, that’s totally fine. But then your primary focus should be on improving your skills so that people want to hire you.

Some final pointers and ideas, especially if you’re having a difficult time:

• Be open to starting with a work trial before you get signed on as an employee.

• Be open to being an independent contractor (at least for a period of time).

• Don’t be afraid to do some unsolicited free work (e.g. if you’re a writer, sending them over content ideas).

• Email VCs and tell them you like their portfolio company and think you could be valuable.

• Don’t let your hopes get too high until you have literally signed an employment contract.

• If you’ve emailed 100s of companies and have had no luck, reread through this guide and audit each step of the process. There’s a big difference between “none of my emails got replied to” and “I had 7 calls but everyone ghosted me afterwards”, and they can teach you about what to improve on.

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