Should you apply or contact the startup founder directly?

Should you apply, or contact someone directly?

Both, every time. Apply through the careers page, then contact a human as well.

These are not alternatives. Applying puts your CV where they can find it. Reaching out is what makes them go and look.

Think about it from the founder's side. They have an email address, a LinkedIn account and a job slot, and all three exist because they want to reach as many people as possible to find the best one. Someone who goes out of their way to start a conversation is showing them exactly the behaviour they are hiring for. It is not going around the process. For an early-stage company it is the process.

The same holds at Series A and beyond, it just changes who you write to. A talent lead, or the head of the function you would sit in.

How many applications does a startup role get?

It varies enormously, but a recently funded, well-known company hiring an early role can get into the hundreds or thousands.

Volume tracks credibility and timing. A YC-backed company that has just announced a seed round and is hiring a founding engineer will be buried. A quieter company hiring its fourth salesperson might get twenty applications.

This is the whole reason direct outreach works. In a pile of six hundred CVs, being slightly better on paper changes nothing. Being the one person who wrote to them changes everything.

Who actually reads applications at a startup?

At an early-stage company, a founder does. Usually the CEO, CTO or CPO depending on the role.

There is no recruiting team and often no recruiter at all. The person deciding whether to reply to you is the person who will be your boss, and they are reading applications in the gaps between everything else they are doing.

That is good news and bad news. Good, because there is nobody filtering you out by keyword before a human sees you. Bad, because the human has thirty seconds and four hundred other CVs.

How long does a founder spend on one application?

Under a minute, and often closer to thirty seconds.

Thirty seconds is a skim, not a read. They are looking for one thing that makes them stop, and if they do not find it they are on to the next one.

It follows that anything requiring careful reading to appreciate will not be appreciated. A full page of cover letter is not read. A CV where the interesting thing is in the third bullet of the second job is not seen.

If you are reaching out anyway, why apply at all?

So that the moment they are interested, your CV is already sitting there and they do not have to ask for it.

A founder who likes your message will go looking. If you have applied, they can pull up your CV in the same minute. If you have not, they have to reply and ask, which is another day of delay and another chance for the thread to die.

It is also worth mentioning in the message itself. Saying you have just applied through the careers page and wanted to reach out directly gives them somewhere to go immediately.

What if there is no open role that fits you?

Reach out anyway, name the gap, and tell them what you would fix.

An open role tells you the company is hiring and has money to spend. That is useful information even when the role is wrong for you. A company advertising for a founding engineer is a company that has just raised and is about to have a dozen problems that are not engineering problems.

So write to them and be direct about it. You saw the engineering role, you are not an engineer, here is what you have done before, and here is where you suspect their bottleneck is. Then ask what it actually is. Founders are usually happy to tell you, and now you are in a conversation about their problem rather than an application queue.

This works better at early stage than anywhere else, because the roles genuinely are not fixed yet. Someone joining a seven-person company shapes their own job in the first month regardless of the title on the contract.

Find companies that are hiring right now

Recent funding and open roles are the two signals worth filtering on before you write to anyone.

Direct outreach works best when the company is actually in a hiring window. A round announced in the last few months and live openings on the site are the two things to look for, whether or not the listed role is the one you want.