How to Write Cold Emails That Get Replies

TL;DR

Cold emails fail for five fixable reasons, and the first is skipping segmentation: divide your list into three to five segments by company size, industry, role, and location before writing a single line. Keep each email between 50 and 80 words, open with a specific observation about the prospect rather than yourself, and offer value instead of asking for a 15-minute call.

Transcript

If you want your cold email campaigns to get good results, you need to know how to stand out in your prospects inboxes. And I know this because I've sent millions of emails. And through hundreds of split tests, I found that if your reply rate isn't at least 3%, there's only five mistakes that you could be making. But if you can fix those mistakes, ... Read More

Key Insights

• A cold email's only real job is to feel written specifically for one reader and to get that person to raise their hand, not to close a deal. It generates direct response interest by proving relevance in the first 5 seconds and answering what's in it for me immediately.
• Segmenting before writing is the fix for spray and pray outreach. At minimum, split the list by company size, industry, role such as founder or VP or CMO, and possibly location, because a message trying to be relevant to everyone ends up relevant to no one.
• Three to five segments is enough for most lists. For each one, answer four questions: the number one pain point right now, what they care about most such as speed, scale, compliance, or cost, the terminology they actually use, and what proof or value would resonate.
• Inserting a job title is not personalization, it only proves you have access to LinkedIn. Bad personalization is worse than no personalization because it shows the prospect you did not actually care and simply pushed them through a mass send.
• The them first rule says the prospect's company or situation must be mentioned before your own company appears. If you talk about yourself before talking about them, you have already lost the reader because you are irrelevant to them at that moment.
• The only them test asks whether a sentence could apply to a thousand other companies. Lines like noticing three new SDRs from a LinkedIn post or Salesforce with no enrichment in the tech stack pass; wanting more pipeline or growing revenue fails.
• Boomerang's analysis of millions of emails found messages between 50 and 125 words get the highest response rates, roughly 50% higher than longer emails. Around 60% of emails are read first on mobile, where a dense block of text gets postponed and then never read.
• The drunk test is a readability check: if someone could not understand your email in 10 seconds while drunk at a bar, it is too complicated and needs simplifying. Every paragraph should communicate one idea and be scannable on its own.

Questions & Answers

Q: What is the real job of a cold email?

A cold email has one real job: to feel like it was written specifically for the person reading it, and to get that specific person to raise their hand and show interest in what you are saying. Most people wrongly think cold emails are about closing a deal. They are not. They are about generating direct response interest. To do that, the email needs to prove relevance in the first 5 seconds so the reader thinks this person actually knows who I am and what I am dealing with, and it needs to answer the what's in it for me question immediately.

Q: How do I segment a cold email list before writing?

Segment the list before you write a single email. At minimum, segment by company size, industry, role such as founder, VP, or CMO, and possibly location. Divide the list into three to five segments; you do not need to go crazy, you just need to stop blasting everyone with the same message. For each segment, answer four questions: what is the number one pain point right now for that person, what do they actually care about most such as speed, scale, compliance, or cost, what language or terminology do they actually use, and what proof or value would actually resonate with them. Then write a different email per segment. Segment first, then write.

Q: Why does spray and pray cold emailing fail?

Spray and pray is blasting the same generic message to everyone on a big acquired list instead of segmenting by industry, company size, role, or the actual problem the prospect faces. Too many senders treat a 10-person startup the same as a 10,000-person enterprise, or pitch the exact same thing to a CMO and a VP of sales. The problem is that the message is not relevant to anyone because it is trying to be relevant to everyone. Relevance is what earns attention in the first few seconds, and a message built for a generic average reader has none of it.

Q: What makes a cold email opener generic?

The generic opener problem shows up in two ways. First, the email starts by talking about you, your company, and what you do instead of immediately addressing something relevant to the prospect, for example "My name is Austin. I'm the founder of agency. We help agency scale." Second, you think you are personalizing just because you inserted a job title or company name, as in "As the VP of sales at company name, I'm sure you're focusing on hitting your revenue goal this quarter." Nobody cares about you yet, and mentioning a job title only proves you have access to LinkedIn. You have 3 seconds to earn the right to talk about yourself.

Q: How do I test whether my personalization is good enough?

Use a two-part test. Part one is the them first rule: the prospect's company or situation should be mentioned before your company is even mentioned, because if you talk about yourself first you have already lost. Part two is the only them test: ask whether the sentence could apply to a thousand other companies. If yes, it is too generic and needs a rewrite. If no, you have a good personalized line. Lines that pass include noting they just hired three SDRs based on a LinkedIn post, or that they use Salesforce but have no enrichment in the tech stack. Lines that fail include assuming a VP of sales wants more pipeline.

Q: How long should a cold email be?

Keep it under 80 words total, with one to two sentences maximum per paragraph. According to Boomerang's analysis of millions of emails, messages between 50 and 125 words get the highest response rates, about 50% higher than longer emails. Long emails get immediately deleted, especially on mobile where 60% of emails are read first. Dense paragraphs are worse still: a prospect opening a huge block of text on their phone thinks they will read it later, which means never. People scan rather than read word for word, so if the email cannot be scanned in 3 seconds it will not be read at all.

Q: What is the drunk test for cold emails?

The drunk test is the final step in a four-step shortening process. First, write your email naturally without worrying about length. Second, read it on your phone by pulling it up in your email app. Third, apply the rules: break up any paragraph longer than two sentences, cut 30% if the total email exceeds 80 words, and remove any word that does not directly contribute to the core message. Fourth, apply the drunk test: if someone could not understand your email in 10 seconds while drunk at a bar, it is too complicated and you need to simplify it.

Q: Why is asking for a 15-minute call a bad cold email offer?

The ask for a call offer problem is when your entire offer is something like "Can we hop on a 15-minute call?" or "Are you free for 15 minutes in the next couple of days?" You are asking the prospect to give you their time without offering them any value in return first. The prospect does not know you and does not trust you. A better close offers value instead, such as asking whether it would make sense to send over the three-step audit used to fix a problem you identified, noting it takes only 10 minutes to implement on their end.

Summary & Key Takeaways

• A cold email has one real job: to feel like it was written specifically for the person reading it and to get that person to raise their hand and show interest. It is not about closing a deal, it is about generating direct response interest. It must prove relevance in the first 5 seconds and immediately answer the what's in it for me question.

• The spray and pray mistake means blasting the same generic message to a whole acquired list instead of segmenting it, treating a 10-person startup the same as a 10,000-person enterprise or pitching a CMO and a VP of sales identically. The fix is to split the list into three to five segments, answer four questions about each segment's pain, priorities, language, and proof, then write a separate email per segment.

• The generic opener problem covers both starting with yourself and fake personalization that only inserts a job title or company name. Mentioning a job title only proves you have access to LinkedIn, and bad personalization is worse than none because it signals you do not care. Pass the them first rule and the only them test before sending.

• The wall of text trap is any email over 80 words or with paragraphs longer than two to three lines. Boomerang's analysis of millions of emails found messages between 50 and 125 words get the highest response rates, about 50% higher than longer emails. Write naturally, read it on your phone, cut 30% if over 80 words, and apply the drunk test.

• The fourth mistake is making a 15-minute call the entire offer, which asks the prospect for their time without offering value in return when they do not yet know or trust you. A better close offers something concrete such as sending over a three-step audit that takes 10 minutes to implement on the prospect's end.