How to Cold Email a Founder About a Job That Doesn't Exist Yet

In July, one of our clients applied for a customer success job at a small automation consultancy. We updated his resume, wrote a cover letter just for that role, and he sent it in through the usual portal. He didn't get the job.

Later that day, I found the founder's email address and sent her a message. I also emailed the head of customer success. These weren't sales pitches. Each email explained the problem the job was meant to solve, shared one thing he had done at his last job that fit, and made it clear I'm not a recruiter and there was no fee. I attached his resume.

I then asked him to write to her as well, using his own words. He did, but later told me it felt pushy and that he wouldn't have done it on his own.

No one replied. Neither to my emails nor to his.

Six weeks went by with no response

That was it for most of July and August: three emails, then silence. If you've ever sent a cold email and waited for a reply, you know how it feels. It seems like nothing happened, and it's easy to think that's true.

In the second week of August, the company posted a new job for a project manager to handle scope and timelines for client projects. We hadn't seen the posting, and he hadn't applied. But their HR lead reached out to him directly to ask if he was interested.

We put together an application for that job, he applied, and I emailed three people at the company, including the founder again. None of those emails got a reply either.

He had five interviews. The last was with the founder, the same person I'd emailed in July. He signed the contract on Friday and started work the next Monday.

What the email really accomplished

It's easy to think this was just luck: a company opened a new job, and he happened to be in their records. But he was there because two people had put his name in front of the founder six weeks earlier, and one of those people was him.

An application only counts for the job that's open right now. It goes into a stack for that posting and gets filed away when the job closes. The portal won't remember you for the next opening.

But a person does remember. The founder of a 25-person company reads her own email. She might not reply, and in this case she didn't, but she saw a short, specific note about a candidate who had done the work she needed. Then she saw a second email from the candidate himself. When the next job opened, his name was already familiar.

None of the emails got a reply, but every one of them made a difference.

Why people hesitate to send these emails

Out of everything we ask clients to do, sending the email is the step they resist the most, even more than updating their resume or preparing for interviews.

The reasons are always similar. It feels like overstepping or even begging. People don't know who to contact. They assume the founder won't read it, and if there's no reply, they think it failed.

All of those reasons are mistaken, but the last one is what holds people back. Silence after a cold email is normal, but it doesn't mean nothing happened. This is my clearest example, but it's not the only one, not even for this client. In June, we sent an email to a company on his target list. The COO forwarded it to the head of engineering, who invited him to interview. That one didn't lead to an offer. This one did.

How to write an email that gets noticed

If you want to try this, here's what we do and what we told him to do. This fits into our bigger approach: send fewer applications, but target companies you really want to work for.

Pick companies, not just job postings. Choose five places you'd truly like to work, even if they aren't hiring right now. The goal is to be known before a job opens up.

Find the person who would be your boss's boss. At a big company, that's usually a director or VP. At a small company, it's often the founder, and founders usually read their own email. You can often guess their address from the company's email pattern. A few minutes on LinkedIn and the team page can help you find it.

Keep your email under 120 words. Use three short paragraphs: one line about who you are, a sentence about why you chose this company (show you've done your homework), and one thing you've done that would help them. Include a number if you can.

Don't ask directly for a job. Instead, ask to be kept in mind. For example, say, "If something opens up on the delivery side, I would appreciate being considered." That's easy for a founder to agree to mentally. Asking, "Do you have any openings?" is something she has to say no to.

Attach your resume as a file. Not just a link to a drive folder.

Expect silence. Then send another email. Getting a reply isn't the only way this works. In our best example, it didn't work that way at all.

How we help our clients

For our clients, we write those emails ourselves, using our own address to introduce the candidate. Then we ask the client to follow up in their own words. Two emails from two people send a message that one email can't: this person has support, and they're also willing to speak up for themselves.

That's the part of our service that surprises people most. They expect a tailored resume, but they don't expect us to write to the founder. This approach is what led to this placement.

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Shortlisted finds roles, writes applications, and sends emails for $95 a month. If you want us to handle this for you, start here. If you'd rather do it yourself, this is how to reach a person instead of just another pile of applications.