What I Learned After Sending 4,000+ Cold Sales Emails

Cold emailing is a necessary component of any sales and marketing outbound activities you do. Honing that skill takes time and in a lot of cases you learn by doing all the possible mistakes yourself first. What I’d like to do is share what I’ve learned after sending 4,000+ cold sales emails when doing customer development and business development for Crowdlinker in order to help you avoid some common pitfalls. I’ll share the techniques, lessons learned and templates you can use to increase your open and reply rate.

Let’s dive right in.

Understand your customer persona

It is important that you understand your value proposition in order to come up with the right customer persona(s). If you want to get high open and response rates, it is critical that you understand your buyer persona’s needs and pain points. HubSpot has a great blog post on creating detailed buyer personas for your business. After you come up with your buyer personas, you are ready to start architecting your campaigns.

The art of crafting a subject line

Your subject line often determines whether someone will open your email or not, especially when it comes from someone you’ve never met before or heard of. Make sure your subject line summarizes the value proposition and sets expectations properly.

Here are some tips to keep in mind:

Personalize It

People respond better when they see that you took the time to personalize the subject. Keeping your subject personal helps you increase the chances of your recipient clicking on your email, which is half of the battle for people’s inboxes.

Word of caution no using people’s names in the subject. Using their first name in the subject line might seem spammy to some, so only use it when you think it makes sense. From my experience receiving emails with a subject “Andrei, blah blah blah” they were sent using mass email solution where by name in the subject was a dynamic variable that changed depending on the recipient.

Be Specific

Get to the point and don’t waste people’s time. Short and descriptive subject lines generate higher open rates. Remember that a lot of people these days open and action on emails on their phones. Longer subject lines get cut off on smartphones, so this serves as another reason to keep your subjects succinct.

Be Genuine

Nothing smells of “mass email outreach” than an email written by a non-human. You’ve seen those emails. The manner in which they’re written results in a quick turn off. If the sender does not respect my time by failing to writing a genuine email, why would I want to do business with them?

Deliver On The Subject

Make sure your body delivers on what you state in your subject line. If you promise A in your subject line, but deliver B in your message, your open rates might be high, but your responses will be abysmally low. So, stay away from misleading subjects that have little to do with the body of your email.

Avoid Buzz Words

It’s a good habit to refrain from using salesy and marketing jargon, so as not to alienate your reader or sound sound too salesy. Words like “sale”, “buy”, “free”, “sale”, or “reminder”, as well as exclamation points and all caps can potentially trigger a spam filter.

Test Test Test

It’s always a good idea to A/B your subject lines on a small pool of recipients first before sending the winning subject to the other 90% of recipients. Say you have a list of 1,000 people. Send 50 emails with subject A to control group A and another 50 emails with subject B to control group B. Get the results and send the winning subject to the other 900. Get into the habit of testing in order to backup your decisions with data as opposed to intuition.

Track Track Track

There are a plethora tools out there that allow you to track your open rate, click through rate, optimize your subject lines. Examples include Outreach.io, ToutApp,PersistIQ, SalesLoft, Reply. Use those tools to track key metrics that will help you optimize the performance of your outreach campaigns.

Here are some examples of effective subject lines:

“Introduction: Richard”
“Introduction: Jeff <> Richard”
“Introduction: AP CRM <> MagnetIQ”
“Quick request”
“Trying to connect”
“{Name of their company}”
“30m interview to be featured on Blog Name”
“Conversation about marketing your brand to a 300K audience”
“Customer acquisition strategy for KJM Interactive”
“3 ideas for KJM Interactive making $1M/mo in MRR”

Here are some not so effective subject lines:

“Partnership opportunity”
“Chat about working together”

How to structure your message

Don’t waste your recipient’s time. Get to the point in a succinct manner. Lose all the fluff that adds unnecessary information.

Here’s a structure you might want to consider implementing:

1. Greeting

Make sure you personalize your greeting, whether you’re doing it manually or using an email automation tool. More on examples of such tools below. According to Experian’s 2013 Email Market Study, personalizing your email will increase your open rate by 26%.

2. Connection statement

The connection statement is a way to relate you to the target.

  • Did you meet at or attend the same conference?
  • Did you read their blog? How did you learn about them?
  • Is there something really interesting about their business to you?
  • Is there something interesting or impressive about their website?

If you don’t have a statement to fit this mould, then do more research until something falls into place.

3. Praise

You should include some form of authentic praise in your initial communication. It can be included as part of the connection statement, but authentic praise can be a positive element. Make sure you are as specific as possible to stay away from sounding hollow.

Example Openings:

I was at CES too last week, but I was fully booked. I wish we had met there, so we could talk about the way you deal with online orders now. Your success in 2015 has been really impressive.
I found your website last week and I was impressed. Is it your primary marketing channel?
I saw an article on Entrepreneur.com about your recent launch of XYZ. Congrats! There’s a definitely a gap in the marketplace that your product can fill.

4. The Ask

Example Pitches:

I run a blog that highlights exceptional real estate outfits and I’m writing to see if you would be interested in a 30 minute interview via Skype or phone?
I would like to schedule a 20-min call to ask you some questions as part of research I’m conducting into tier 1 challenges digital marketers face on the job. I’ll use that information to form a problem hypothesis for a software product my company is developing.
I’d appreciate if you could schedule a time/day convenient for you by clicking here: johnsmith.youcanbook.me
Our product helped similar companies in your niche increase revenue by 30% in 2 months. Do you have 15 min on Wednesday at 11am to jump on the phone to discuss further?
We help small business owners like you who are frustrated that they can’t track the ROI of their marketing activities and are disappointed that they can’t figure out where their buyers are hiding. Does that resonate with you?
I would like to learn how your company generates sales leads to determine if there might be a good fit for our solution. We’ve been able to help clients like XYZ generate 30% more qualified leads in 3 months.
Can we find 5–8 minutes to chat about this next week? Here’s my availability: johnsmith.youcanbook.me
Can you refer me to the right person within your company responsible for outbound sales?

It’s important that you keep that task specific. Don’t ask your recipient: “What do you think of my proposal?”, because she might not have the inclination nor the time to write all of her thoughts on your proposal in an email. Instead, she’ll just delete your email or ignore it.

Instead, you might ask: “Are you the right person at XYZ Corp?”. This way, if the person you’ve emailed is not the right individual, they’ll be able to forward you to the correct person within their organization who you should be talking to.

5. Close


“Thank you”
“Thanks in advance”
“I look forward to meeting you”
“Best of luck at Global Expo ’16”

6. Signature

Customer Development Sample Email:

Hi Ashley,
I found RazorFish’s latest blog post on the best practices in digital marketing really insightful. I passed it on to my colleagues in marketing.
I’m working on a product to help marketers like you increase awareness and branding in the eyes of your customers. I want to make sure we’re solving a real tier 1 problem and are on the right track.
If you are using social media to build awareness for XYZ, I would appreciate your help and advice.
Do you have time to give me some advice over a 15-min call? I’d appreciate if you could schedule a time that works best for you by clicking here:
Andrei Arkhanguelski

Business Development Sample Outreach Email:

Hi Ashley,
I found RazorFish’s latest blog post on the best practices in digital marketing really insightful. I passed it on to my colleagues in marketing.
I looked at XYZ’s social media profiles and you don’t seem to be posting frequently. Is it a matter of lack of capacity or is it that social is not a priority for lead gen?
We recently helped a 50-employee company in the same space as you start generating 10 qualified leads per week as a result of implementing our social media solution.
Do you have 15 on Wednesday at 11am to discuss if our solution is a good fit for RazorFish?
Andrei Arkhanguelski

Do a Quick Sanity Check Before Hitting the “Send” Button

Lincoln Murphy has a good roundup of 7 sanity checks for sending cold emails. Go ahead, read it and make sure your tone is right, your message is succinct and to the point and please optimize it for reading on a mobile device. Below, you can see why it’s important.

Optimize for Mobile

It’s no surprise that optimizing your emails for mobile is no longer optional. It’s a must. From 2010 to 2015, email opens on mobile devices increased by 30% according to Campaign Monitor.

Litmus confirms a similar trend. As of 2014, open rates were at 22% for desktop, 25% for webmail and 53% for mobile.

A/B Testing

When I was doing outreach to media executives in North America as part of customer development for a product we were trying to validate the need for, I decided to do a little A/B test. A/B testing is a great way to test your messaging. Campaign Monitor estimates that A/B testing improves conversion by 49%.

In my limited email campaign of emails sent to a total of 400 people, I sent 200 emails to control group A and another 200 emails to control group B.

Group A Email:

Out of the 200 recipients in group A, 50% opened the email, 11% clicked on the link and 5.5% replied back.

Group B Email:

Out of the 200 recipients in group B, 48% opened the email, 8% clicked on the link and 2.5% replied back.

It’s not clear what exactly resulted in higher open, click-through and reply rates in control group A, but I can guess that it could’ve been a clear ask: “15 min of one’s time” in template A vs. “a few minutes” in template B.

Some would argue that my example above is not a proper A/B test, because for an A/B test to be valid only one variable at a time should be changed to determine the cause and effect. The results of my A/B test are not radically different. I can attribute it to the fact that both templates are more-or-less similar.

I would suggest you start off with 2 different templates and do A/B testing by sending it to 5–10% of your pool. Keep the subject line the same if you’re testing the body to make sure you’re only measuring one variable at a time.

Once you get a clear winner, take it and modify it slightly to conduct the next A/B test. This second A/B test will help you understand whether slight changes in wording (e.g. “15 min of your time” vs. “a quick phone call”) make a significant different. Test it on the following 5–10% of your pool and once you get a winner, send the winning template to the remaining 80–90% of your target list.

Email Automation Tools

It’s no secret that if you were to do email outreach manually, you would not be able to reach as many people as you can at scale. Email automation tool enable modern marketers to easily set up email sequences to send personalized, timely, and relevant emails to customers and not-yet-customer through drip campaigns.

I recommend you check out the following email platforms for automating your cold email outreach:

For small batches of emails you might want to consider using a simple mail merge solution like Gmass. I’ve used it for batches of 20–50 people and it’s been great.


You might be surprised, but it might take you 7–8 follow-up emails to get a response from a prospect. Here’s are some tips to ensure that you’re being persistent in your outreach:

Make a dumb joke in your follow-up note. Say something like “I know you were busy skydiving in Dubai last week, so I thought I’d check back this week.”

Mix up your message. Avoid sending the same email again. Paraphrase it or use a different angle. Also, don’t ask “Did you receive my previous email?”. That’s just lame.

Try a new approach. Say something like “Maybe that wasn’t the most exciting pitch. Here’s a couple other ideas I’d love to run by you.”

Consider using the following cold email follow-up sequence recommended by Steli Efti, Founder of Close.io to ensure that your emails do not fall through the cracks:

Day 1: Send your first cold email.

Day 2: 1 day later send a modified version of your initial email. Phrase it in such a way, so that it conveys the same message, but in a different way. For instance, you could write a 3-sentence body instead of 2–3 paragraphs and vice versa if applicable. Make sure you convey the same message to stay consistent.

Day 4: 2 days after you send your 2nd follow-up email send a succinct and brief email restating your ask. It can be to refer you to the right person, schedule a call or reply to your email. Make sure it matches the ask in your original email sent on day 1. You could say something like: “Hey Bob, following up on my email from Feb 15th. Would love to discuss the suitability of ZoomShifter’s solution for NexGen. When would be a good time to discuss over a quick 10min call? How about Wednesday, Feb 21st at 1pm Eastern?”

Day 9: Out comes the breakup email. You can read below how to properly use one, but essentially you’re going to communicate to the recipient that you’re going to stop emailing her after this last email. By doing this, you’re betting on the psychological principle called “loss aversion”, which describes people’s tendency to much rather avoid a loss than to acquire a gain.

How to use a breakup email

Once you’ve emailed someone 5–7 times and haven’t heard back, send them a breakup email. Crafted the right way, it’s one of the best ways of getting a positive response. This tactic works both for outbound emails (when you’re sending emails to people who have never expressed an interest in your offer or interacted with you) and inbound emails (when you’re sending out emails to people who have at some point expressed interest in your offer, e.g. by signing up for a trial).

Here’s an example:

Subject: Goodbye from PurpleGecko

I was really looking forward to explore an opportunity for PurpleGecko to help XYZ Cop increase the quality of inbound leads, but I haven’t heard a response to my emails and phone calls.
I’m guessing the interest is not there on your part, so this will be my last email to you. I’d be happy to speak with you when you are ready to invest resources into a lead generation solution.

Once again, I’d like to point to Steli Efti as he does a great job explaining how to use breakup emails.

Complying with the CAN-SPAM Act in the U.S.

Unsolicited commercial email is a grey area when it comes to complying with anti-spam laws. There are a bunch of companies that will sell you email lists, but it’s never a good idea. While this may be technically legal, it often damages your reputation and the reputation of your email marketing company. As such, this sort of behaviour is usually not allowed in their terms and conditions. Companies like MailChimp, Campaign Monitor and Customer.io have clear guidelines surrounding spam and require people to have opted-in to be emailed.

What constitutes an opt-in?

Ideally, you want to have a double-opt-in process in place. Here’s how it works:

  • Someone fills out a form by giving you their email address,
  • You send a one-time confirmation email asking them to click a link and confirm their email address.
  • If they do it, they’re opted in. If they don’t confirm, you do not have their permission to email them.

This works great for newsletters or any ongoing emails that you’ll be sending with updates from your site. Here’s an example of what an opt-in form looks like:

For your reference, there’s an interesting thread on Quora on the distinction between a spam email and a cold email. I suggest you take a look at it.

The CAN-SPAM Act in the United States clearly stipulates that if your message contains only commercial content, its primary purpose is commercial and as such, it must comply with the requirements of CAN-SPAM, which are:

Don’t use false or misleading header information. Your “From,” “To,” “Reply-To,” and routing information — including the originating domain name and email address — must be accurate and identify the person or business who initiated the message.

Don’t use deceptive subject lines. The subject line must accurately reflect the content of the message.

Identify the message as an ad. The law gives you a lot of leeway in how to do this, but you must disclose clearly and conspicuously that your message is an advertisement.

Tell recipients where you’re located. Your message must include your valid physical postal address. This can be your current street address, a post office box you’ve registered with the U.S. Postal Service, or a private mailbox you’ve registered with a commercial mail receiving agency established under Postal Service regulations.

Tell recipients how to opt out of receiving future email from you. Your message must include a clear and conspicuous explanation of how the recipient can opt out of getting email from you in the future. Craft the notice in a way that’s easy for an ordinary person to recognize, read, and understand. Creative use of type size, colour, and location can improve clarity. Give a return email address or another easy Internet-based way to allow people to communicate their choice to you. You may create a menu to allow a recipient to opt out of certain types of messages, but you must include the option to stop all commercial messages from you. Make sure your spam filter doesn’t block these opt-out requests.

Honour opt-out requests promptly. Any opt-out mechanism you offer must be able to process opt-out requests for at least 30 days after you send your message. You must honour a recipient’s opt-out request within 10 business days. You can’t charge a fee, require the recipient to give you any personally identifying information beyond an email address, or make the recipient take any step other than sending a reply email or visiting a single page on an Internet website as a condition for honouring an opt-out request. Once people have told you they don’t want to receive more messages from you, you can’t sell or transfer their email addresses, even in the form of a mailing list. The only exception is that you may transfer the addresses to a company you’ve hired to help you comply with the CAN-SPAM Act.

Monitor what others are doing on your behalf. The law makes clear that even if you hire another company to handle your email marketing, you can’t contract away your legal responsibility to comply with the law. Both the company whose product is promoted in the message and the company that actually sends the message may be held legally responsible.
For CAN-SPAM what matters the most is the primary purpose of the message. There are distinct types of emails:

Commercial content — which advertises or promotes a commercial product or service, including content on a website operated for a commercial purpose;

Transactional or relationship content — which facilitates an already agreed-upon transaction or updates a customer about an ongoing transaction; and

Other content — which is neither commercially nor transactional or relationship.

To help you understand the difference between commercial and transactional messages, transactional or relationship emails consists only of content that:

  • facilitates or confirms a commercial transaction that the recipient already has agreed to;
  • gives warranty, recall, safety, or security information about a product or service;
  • gives information about a change in terms or features or account balance information regarding a membership, subscription, account, loan or other ongoing commercial relationship;
  • provides information about an employment relationship or employee benefits; or
  • delivers goods or services as part of a transaction that the recipient already has agreed to.

Still not sure if your email might be classified as spam? HubSpot’s “12 Signs Your Cold Sales Email Is Actually Spam” blog post might provide more clarity.

Complying with the CASL in Canada

Keep in mind that if you’re a US company conducting an outbound email campaign to Canadian recipients, CAN-SPAM does not apply. Instead, you’re subject to Canada’s Anti-Spam Legislation (CASL). Spam laws tend to be based on the recipient’s location, rather than sender’s country.

CASL applies to anyone, including a corporation, that sends a “commercial electronic message (CEM)”, which is broadly defined and would capture any message sent by any means of telecommunication, be it email or SMS. See CASL FAQ for more context. If you use MailChimp, they were kind enough to put together a CASL-specific guide for you.

To send a commercial electronic message (CEM) to an electronic address, you need to ensure the following:

1. Have the recipient’s consent: You must have a form of valid consent. According to CASL, consent can be obtained either in writing or orally. In either case, the onus is on the person who is sending the message to prove they have obtained consent to send the message.

As per the Compliance and Enforcement Information Bulletin CRTC reserves the right to send you a request for consent and recommends you log the following to make tracking or recording consent easier:

  • whether consent was obtained in writing or orally,
  • when it was obtained,
  • why it was obtained, and
  • the manner in which it was obtained.

2. Clearly identify yourself and your organization. You must include your mailing address. You must also include a phone number for accessing an agent or a voice messaging system, an email address, or a web address for you or the person on whose behalf you are sending the message.
Here’s what a CASL-compliant signature would look like:

Kirstin Carter
Customer Success Specialist @
LinkedIn · Twitter · Facebook · Blog
123 York St, Toronto, ON M5B2G7, Canada
If you do not want to receive further emails from PurpleGecko, click here

3. Unsubscribe mechanism: Provide an unsubscribe mechanism that is functional for 60 days. CRTC considers that an example of an unsubscribe mechanism that can be readily performed is a link in an email that takes the user to a web page where he or she can unsubscribe from receiving all or some types of commercial electronic messages (CEMs) from the sender. Here’s an example of what it might look like:

4. Truth in advertising: Your messages must not be false or misleading. They must not have false or misleading sender information, subject matter information, URLs and/or metadata.
If you need a checklist you can print out and put up on a wall in your office, Constant Contact’s got you covered (PDF). Note that if you happen to willingly violate the anti-spam regulations of your jurisdiction, here’s an interesting discussion on the perils of sending out tens of thousands of mined email addresses.

I hope you found this post informative and useful. I would appreciate if you could share it on Facebook and Twitter.

If you enjoyed reading this post, hit the heart button below. It would mean a lot to me and it helps other people discover the story. If you also share it on social media, I’d be incredibly thankful to you!

Andrei Arkhanguelski is a technology entrepreneur, product designer, online marketer, foodie, and happy dog owner. Besides, Medium, he shares some awesome entrepreneurship-focused content on Facebook, Twitter and YouTube.