The Ultimate Guide to Hacking Cold Emails

16 min readJun 13, 2017

For many people, cold emails are a combination of a hot potato and a tough nut. They would rather avoid it or let someone else deal with it. And honestly, I don’t blame those people, because the entire situation is awful. Sending an email to someone you don’t know and often ask for something (meeting/guidance) — the thought itself is intimidating.

However, if you’re an entrepreneur or a Product guy who wishes to validate a new idea, you must reach out to potential customers. The ideal situations are when you know the potential customer in person, or you know someone in the company who can introduce you to the stakeholder you wish to meet. But what if you must speak with someone in a company where you don’t know anyone?

In this post I will take a very specific use case — sending an email to someone you don’t know, for the purpose of problem validation interview (aka Customer Development) and walk you through the techniques of:

How to find companies that are relevant to problem you wish to validate?
How to find the relevant persona in that company (name + email)?
How to draft an appealing cold email?
The importance of following up on a cold email.

Lets Go!

First, let’s lay out the context:
(1) You’re an entrepreneur and you just had a great idea of a new product or service; or
(2) You work for an established company and have an innovative idea, what should be your company’s next raising star —
Either way, you read steve blank, Ash Maurya and Justin Wilcox blogs/books and you know that you have to get out of the building and speak with potential customers.

1. How to Find Relevant Companies

These are the tools I normally use, when I am looking for companies in a specific domain (i.e. cyber security for enterprise, software testing tools for SMBs, etc.):

Mapme

Mapme has developed a great platform to allow communities map themselves. There are quite a lot high-tech communities that have created a map using that platform, such as: mapped in Israel, mapped in NY, mapped in Ukraine, mapped in Holland and many more. So just look for the map that is most relevant to you.

They all have a similar UI. On the left you can look for companies in specific domains, such as: e-commerce, web, mobile and also specific enterprise companies. When you click on a company, it shows where’s their office located and some basic information. My next step would be to go to their website and see if it meets the profile I’m looking for.

VC portfolio

Another great source I am using to find relevant companies, is the Venture Capitalist’s portfolio. Most VCs update their website with the companies they’ve invested in. The reason I like this resource is because normally the company list will be sorted by category/technology, so it’s easier to search for companies that meet the segment.
In this case, I am looking at google ventures and if I’m looking for enterprise companies, potentially, I have a list of 50+ companies to review.

Competitors

Next would be competitor’s website where some of them list their customers. Each of these customers could be a potential candidate for an interview, which in terms of customer development is priceless! You may have a chance to hear from a customer, how does the competitor product work? Is it any good? And if so, what’s so cool about it? And if it’s bad, why isn’t he happy?
You can leverage this information in order to polish your Unique Value Proposition statement and better position against competitors.

Just Google it

Lastly, if you can’t find companies or if you wish to find more, just google it. For example, try “top 20 cyber…” and google will auto-complete the rest.

2. How to Find a Relevant Persona in the Company

At the end of step 1, I have a list of relevant companies (and their domain name). Now it’s time to move to the next step — finding relevant persona in these companies.

LinkedIn

LinkedIn is the obvious social network to look for people in a specific company. You can use the advanced search to look for a specific position in that company.

For example, if the persona I am looking for is an ‘account manager’ in a software enterprise company, I will write ‘account manager’ as the current position, and ‘Microsoft’, for example, in the company name.

As you can see, I get immediate results:

CrunchBase

Another tool I’m using to find out who’s on the company team, is CrunchBase. CrunchBase is a huge crowd source database that holds a list of more than 650k profiles of people and companies. What’s great about CrunchBase is that it not only shows the company team members, but also the number of funding rounds the company had and how much it raised to date. This is relevant mostly for small-mid companies you’re evaluating, to see if it’s even relevant to approach them.

“The Team” page on the company’s website

Another option, which works well if you’re looking for small/medium companies, is to look for the person under the Team or Management web page.

3. How to Find the Persona’s Email Address

At the end of step 2, I have a list of personas, companies and their domain name. The next step would be to find the persona’s email address.

FTL

Find That Lead , or FTL in short, is probably one of the easiest tools out there. It’s a chrome extension and in order to activate it, you should open the LinkedIn account of the person you want to reach. In this case, I was wondering what’s Kevin Systorm’s email address . The only thing I had to do is to click on FTL icon and it automatically searched and found the email address:

Email Hunter

A similar tool is called Email Finder. It is not limited only to LinkedIn, as FTL, however, the Chrome extension adds an orange button which appears on the prospect’s profile. So, if you feel that you’re up to sending a brilliant cold email to Noah Kagan, his email address (with 67% confidence), is:

Using FTL or Email Hunter is kind of finding email addresses on auto pilot, which is awesome. However, sometimes you’ll have to work a bit harder in order to find the correct email address.

4. How to Validate an Email Address

Rapportive

The first tool I’ll talk about is Rapportive. It is a free browser plugin, available as a Firefox add-on and as a Chrome extension. It basically replaces the adverts in Gmail’s sidebar with useful information about your contacts: a photo, bio and links to social media accounts (Twitter, LinkedIn, Flickr, etc.). The key here is nailing down the contact’s exact email address.

UPDATE (August 2021): Rapportive was terminated. Use Clearbit instead. Whatever is written below applies to Clearbit as well. Enjoy :-)

By now, you know the contact’s name and company domain. All you have to do is to compose a new email on Gmail, and try few variations of the possible email address. Each company has its own format, but typically if it’s a small company it will probably be firstname@domain, while if it’s an enterprise it would be firstname.lastname@domain.

If you nail the right email address, you’ll see the contact info on the right (me, in this case):

Rapportive was able to validate my email address

If you don’t see the contact details, just keep trying other combinations.

TIP: User Email Generator, featured by MailTrack.io, to generate a number of email combinations

But there’s a catch…

Rapportive, which was acquired by LinkedIn a few years ago, uses LinkedIn’s database to look-up the email addresses. In other words, if the contact you’re looking for didn’t update his/her work email address on LinkedIn, Rapportive won’t find it. As you can see below, I wrote down a valid email address of mine (I’ll prove it in few paragraphs :) ), which I didn’t update on my LinkedIn account and Rapportive wasn’t able to validate it. So in theory, you may think it’s not my correct email address…

Rapportive can’t validate email addresses that were not added to the LinkedIn account

So here are 2 tools which can help you figure out the possible email format that is being used in certain corporations.

emails4corporations

emails4corporations.com is a huge repository which, according to the name, lists corporations and the common method of their email format.

For example, if I want to reach someone at Amazon, chances are that the email address is the first-name-initial+last name@amazon.com

MailTester

MailTester is a cool website that checks the email address against its mail server. As you can see, my email address, which Rapportive failed to find on LinkedIn, is actually a valid email address :-)

What did we learn from that example?

If you can’t nail the email address using Rapportive, but Mailtester confirms the format suggested by emails4corporations or mailtrack.io, chances are that this is the email you’re looking for.

“And what if I can’t find the email address?”

Rapportive doesn’t guarantee a 100% success. So if for some reason you can’t extract the email address, here’s what you can do:

Google “@domain”. You may find the email address of other employees and match the email format.
Try to Google the name and review the results
Look for blog posts
Look for YouTube videos
Look for slideshare slides
Look for GitHub projects
Look for tweets (see the next section)
Try engaging via twitter. Follow the person, commant, Love his tweets. Then try sending a tweet with your ask
Try to find another contact in that company
If it still doesn’t work — Move on. Look for someone else or for another company

At the end of this step, you’re ready to start sending emails to the contacts you found.

5. How to Draft a Cold Email

Let’s talk about best practices to draft a cold email.

The 3 basic guidelines are:

Keep it short! No one likes reading long emails from strangers.
Be specific. Explain exactly what are you looking for and what do you want.
Make it personal. Show them that there is a real person behind that email, who made a research and some homework before he reached out.

Now, let’s dig in:

Subject Line:

The more specific and to the point, the better. For example:
Subject: Node.js remote debugging at [company name]
will probably work better than
Subject: Would love your feedback
Mentioning the person’s name in the title is also something that worked out well for me (= better response rate). For example:
Subject: John, maybe [my company name] can solve your [problem]

2. Keep the email short: no more than 4–6 sentences.

3. Spare the long a boring introduction: don’t waste a sentence by focusing on yourself and what’s your position. You’re probably emailing from your work email and include your title in the signature, so the receiving party will understand who are you and where do you work.

4. Make it personal: This is probably the most important advice and at the same time, this is where you’re going to spend most of your time when you’re sending a cold email (depending how anxious you are in getting this guy’s attention).

Remember that you’re emailing a person! Try to refer to something they wrote/shared or a speech they made, etc. It shows that you spent some time doing a research and personalized the email, rather than spamming.
If you got his/her email address from a referral, this is the place to mention it.
You may also want to mention that you’re contacting him/her because you realize they are experts in their domain. Wouldn’t you be curious to read further if someone you don’t know just said you’re an expert? I know I would.

5. Links: you may add relevant links to a one-pager or a video. Also add links in your signature to your social networks. It’s also important for analytics (we’ll see later why).

6. Be specific with what you need:
“I would love to meet you for a short (30–45min) interview” will work better than an open ended “please let me know what you think”. Nobody has the time to tell you what do they think over an email.
I would be even more specific and suggest the exact date/time for our meeting: “How about Tue, Aug 2nd at 4pm?”
It leads to a better engagement because you spare the hassle of figuring out when would be a good time to meet. If the proposed schedule doesn’t work for your contact, he/she will probably offer an alternative schedule.

7. Mention that you’re NOT selling anything:
Imagine that you’re getting 2 emails from 2 different people you don’t know. One is asking for your time in order to show you a demo.
The other says he contacted you because you’re an expert and is asking for a short meeting in order to get YOUR advice on a project he’s working on.
Which one you’re more likely to pay attention to? Wow! The latter just called me a pro… I know I would speak with him first.
Remember that and don’t forger to mention it in your email.

Email Template Example

Here’s a suggested email template that worked for me:

Hi [name],
I was referred to you by [name], who said you are expert in [specific domain].
And/Or
I am writing you because I recently read your blog post about [subject] and it seems like you’re an expert in this domain.
We’re currently working on a [service description 4–6 words] designed for [describe the segment].
But before getting too far ahead of ourselves, we wanted to make sure other customers share these problems and see whether this was a product worth building.
For that purpose, I would love to have a short interview (~45 minutes) to help me understand your current workflow.
Does sometime this week (e.g. Thursday 3 PM) work for you?
I‘m not selling anything, just looking for your advice.
Thanks,
[name]
[title]
[company]
[social links]

6. The Importance of Email Tracking

Earlier, I mentioned LinkedIn as a resource to find relevant prospects, however, I would not recommend sending the email directly from LinkedIn, for the following reasons:

If you don’t have the premium account, you have a limited amount of inmail messages. even with the premium account, you’re limited to ~15 emails
Analytics! If you can measure it, you can improve it.
Knowing whether the recipient has opened the message you sent, or clicked on a link you added to the message, will help you determine what should be your next step, for example, when to send a follow-up email.

For that reason, I prefer using Gmail or Outlook to send the emails, using special tracking tools.

Outlook Tracking Tool — HubSpot Sales

HubSpot Sales (formerly Sidekick) is a great tool for tracking. It works both with Gmail and Outlook and is really cost effective if you want to move to the pro plan.

With HubSpot Sales, you know exactly what happens after you click the send button. Did the recipient open the email? When? How many times?

It also shows whether the recipient clicked on a link in the email, which in my opinion is a better metric than ‘opened’.

Open Rate vs. Click-Through Rate

Tracking email opens, or ‘open rate’ depends on the recipient email client because it’s counted when images load in the recipient’s email. And what if someone doesn’t allow images to load by default? For that reason, the link click, aka click through rate, is more accurate because it depends on the recipient action. It will also shows that people are interested enough, that they engage further.

HubSpot Sales for email templates

Another great use of HubSpot Sales is it’s email template function. If you’re about to send the same email to multiple contacts, you can build a single template and then personalize it accordingly.

Gmail Tracking Tools

Gmail has even a wider selection of great email tracking tools, which similar to HubSpot Sales, they notify whenever someone opens your email or clicks on a link. In this category you can find: HubSpot Sales for Gmail, Yesware, Bananatag, DoubleTick, or my favorite Mailtrack.

7. Follow up Email

Follow up emails are very important and statistically, they get a higher response rate than the original email.
Let’s put things into perspective: in software industry, the average open rate is ~22%, out of those, if you get 10% response rate, you’re really lucky.
Not doing a follow up, is like leaving money on the table — you already made the effort to find the contact you think is relevant, found his/her email address, sent the email, so why not taking the extra mile and doing a follow up?
You simply have to do it wisely and remember that you’re emailing people with a different agenda than yours. They have their own tasks and sometimes your email, no matter how well it’s written, is being forgotten. Follow up simply helps bringing your email to the top of the list and you know what? It also shows that YOU are a human too.
And remember, the fact that someone didn’t reply, doesn’t mean that it’s game over and it’s definitely not personal.

Follow up Guidelines

Email analytics improves follow up results. If you’re able to measure your email performance, then you can do a targeted follow up, because your contacts will be segmented. Those who didn’t open, those who opened but didn’t reply or clicked, etc. A different follow up is required to each segment.
The follow up email should be shorter than the original — don’t provide more info and don’t follow up with attachments or links.
Personal follow up shows that your email was not a spam. Look for something personal, and use it in the email opening. For example:
“I know you were probably busy at [conference name] last week”
DON’T CC anyone.

Follow up Templates

Here are 2 follow up templates you can use, which worked out for me:

1st follow up:

Hi [name],
I didn’t hear back from you last week when I was looking for the appropriate person to [statement in the context of what you’re looking for].
I know you were probably busy with [travel/show/sales meetings, etc.] and I value your time. (optional)
If it makes sense to talk, let me know how your calendar looks. If not, who is the appropriate person?

2nd follow up (in case you didn’t receive an answer):

Hi [name],
I have tried to get in touch with you to see if [statement].
If you are not interested or there is another person you would like me to follow up with, please let me know.
Would it make sense to invest 5–10 minutes to determine if there is a mutual fit between your [statement] and the product we wish to develop? If not, who do you recommend I talk to?

8. A/B Test As Much As Possible

Sending the same emails over and over and getting the same (bad) results, doesn’t make sense. It took me a while to test many variations until I realized what works best for me. And BTW, I constantly test email variations — chances are that a year from today my recommended template would look completely different.

The concept of a/b testing is very simple, although it requires patience:

Send email template to group A
Send email template to group B, with ONE modification. It can be a slightly changed subject line, or a completely different one. It can be a different email opening, etc.
Measure which variation converted better (open rate / response rate).
Repeat

Summary

Cold email is a great tool which may help you reach out to people you don’t know in order to get something. Like any other tool, in order to use it properly you have to ‘read the manual’ and make sure you follow the guidelines. It also helps to read the email out loud before you send it, and try to figure out:

Is that an email you would reply to?
Would you meet that person? Does he offer something that is worthwhile for you?
Did it take you more than 30sec to read it? if so, it’s too long!
Is it a personal email? Or can the recipient feel you’re sending the same email to a bunch of other people?
Is there a clear ask at the end?

Resources that inspired me

Wanna learn more about cold emails? The internet is full with great blog posts and with recommended best practices. Here are the blog posts that inspired me in my work and in writing this post:

PS — I have 2 simple asks for YOU

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