How to get hired at a startup

A straightforward strategy for landing a job at a startup

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Below is an approach to getting hired at a startup that I’ve now seen dozens of people use successfully. There’s no magic—it’s just a simple strategy that, if taken seriously, could *actually* change your life. Hope it helps!

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Sometime during the real doldrums of sophomore year of high school, my career counselor sat us all down and whipped out a 72-page Powerpoint presentation 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 hopefully 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.

Before we dive in, a few disclaimers: 1) Beware of fully outsourcing this decision (you should work on whatever you want!), 2) most startups aren’t very good at most things, and 3) working at a startup is probably not your easiest path to becoming wealthy.

With that out of the way, here’s our best advice for getting a job at a startup.

By the way, one of the best ways to improve your odds of getting hired is to practice writing. If you’d like to improve your writing (which may help you get hired!), consider joining our Writing Club. It is like a run club, for writing (filled with loads of interesting startup founders, engineers, writers, and more). You can join for a discount here (and use the code “nextplay99”).

How to actually get hired at a startup

There is one clear path to increase your odds of being hired by a startup: try much harder than anyone else who applied.

This sounds obvious. Yet practically nobody does it. That’s because trying harder than any other applicant is, by default, not easy. It’s going to take some work. But the payoff is that you get to take more control over the future of your career and life, and we think that’s worth it.

Consider the base case: most people just apply to jobs by sending their resume (and maybe a cover letter).

If you really want the job, we suggest you try 10x harder than those people. That’s not an exaggerated number — we mean 10x. Trying only 2x harder, for example, might mean you just send a short email to the founder when you apply, letting them know that you applied and that you’re interested. That’s okay. But you can do a lot better. To get you started, we wrote a list of things you can use as inspiration. These are things that have worked to land people interviews (or to get them hired) at startups.

If you copy this list 1:1, you are not trying 10x harder. Our goal here is to give you tactics and inspiration, which you can run with and modify based on your individual situation.

• Talk to their customers, collect learnings, and summarize those learnings for them.

• Make a list of ideas that would help the company generate more revenue.

• Make a list, or resume, of your failures.

• Write them a sample plan of what you could (or would) do in your first 30 or 60 days working there.

• Sign up as a customer and build your own “friction log” for them.

• Record a Loom of why you would want to work there.

• Write a short essay, or memo, analyzing their competitors.

• Make a creative slide deck about why you’re the right pick.

• Get them customers.

• If you have an interview, send a great thank you afterwards. More broadly, make sure all of your communications with them are thoughtful.

• Give them feedback on their interview process.

• Ask interesting questions that actually push the interviewer.

• Offer to work for them as a contractor for a few months before going full-time.

• Do some work for them for free.

• In addition to applying, send an email to the founder.

• Ask them why people have quit in the past and then come up with solutions to any issues.

All of these tactics may work. They are not guaranteed to get you hired, but they increase the odds that you will stand out.

The differentiation of this approach is that you are leading with value. 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 less useful because then someone has to figure out what you should do, and that takes work. Those kinds of emails we find get far less replies.

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Finding great opportunities

If you are bought in on the premise—to try harder than everyone else!—the next step you will want to take is to identify interesting opportunities.

An easy way to start this process is to look at some of the lists we’ve shared on Next Play. For example:

• Roles at Sequoia companies, roles at Sierra, venture investor at Bessemer

• Meet the fastest growing startup teams

• Recommendations from Haystack Ventures’s Partner Aashay Sanghvi

• 7 startups Lindsey at Bessemer Venture Partners thinks you should join

Try not to limit your search unnecessarily. It’s totally okay to reach out to companies who have no open roles. It’s totally okay if they say they are only hiring in person and you do not live in that city. It’s totally okay if you are not qualified on paper for the position. These variables may impact your odds—but we think that so long as you’re capable of providing value, rational startups will find a way to work with you.

To take one of the ideas mentioned a bit deeper, consider the following example:

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

Be as specific as possible in your memo about what you would suggest. Real, practical ideas. If your memo reads like it was AI generated, people will most likely be able to tell.

In it, you can try to leverage your unique skills. 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 can be a tool to help you organize your thoughts.

Getting in touch with the company

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

We wrote more details about our suggested approach to emailing here:

One thing you’ll need to do is find an email address. Here are a few quick tips for finding it:

• The founder’s email will usually be firstname@companydomain.com. 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.

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Repeat this process with at least 30-50 startups.

This is the part where you do not give up too quickly. The odds of someone replying to your email depend on a number of factors:

• How much value you could likely add

• If you seem 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.

Note that you’ll want to follow up if people do not 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 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 a bit 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.)

Once they do respond to you, you should aim to respond quickly. 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.

The call

We’re moving quickly here but imagine as a next step from the email, you get on a call with a hiring manager. What do you do? How do you angle the call? There’s probably more details to consider (perhaps for another essay!) but we broadly suggest the number one most useful thing you do is try to figure out the following:

“What’s the most important thing you needing solving right now?”

If you can figure this out, you can angle the remainder of the call towards solving problems and adding value to the company.

A few other quick 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 can feel 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.

If you’ve made it this far, we think there’s a good chance you’ll land a job at a startup (pending you going through the rest of the process with enough companies).

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Getting hired

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:

• 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”.

• Show your gratitude. 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.

• 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).

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

• 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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Thanks for reading! If you’re looking for interesting startup opportunities, check out Next Play.