We've written about cold emailing a lot on this blog. However, I don't think we've ever made a post dedicated to showing you examples of real cold emails we sent. Some of these prospects responded to us, some of them didn't. That's just how it goes sometimes, but we're going to unload them all. I'm going not just to show you the emails, but the thought process behind the copy for each of them starting on LinkedIn.

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But first, the structure of a cold email is important

4 Questions a Good Cold Email Should Always Answer:

  1. How am I special to you? 
  2. Why are you contacting me?
  3. Who are you (specific relevant value prop)?
  4. What do you want me to do with this message?

Alright, let's get started!

Email #1: Telling Your Own Story or Experience.

Using the LeadIQ workflow, you will be looking for context on your prospect by looking at their LinkedIn profile. The first prospect started their career in Quebec working for Just For Laughs.

LinkedIn Career description for Just For Laughs

Not only is this interesting to me because I'm into comedy, especially knowing the great comedy scene out of Canada, but also because I have something I think about every time I see Quebec in life.

See, this is the part of personalization that no one talks about. You need to find your own unique thing you share with that prospect to break in. What I do for personalization shouldn't be the same thing as what you do.

Don't use templates for this kind of outreach. Templates lack context and are not the future of sales prospecting. You need to personalize this type of outreach.

Here's the email that I sent:

"Subject Line: Poutine and ice storms

Hey *****,
Saw on LinkedIn you used to live in Montreal when you worked at Just for Laughs. Funny story for you. When I as in school, I took a culture elective class on surveying Quebec culture, cinema, and history.
At the end of the semester, we were supposed to go there, but Quebec got ice storms and the whole trip got cancelled. I’ll never know the pleasures fresh poutine.
Anyways...I wanted to see if we could talk? We help make it easier for reps to create new. prospects in Salesforce, research them, and sell without leaving LinkedIn. This will help reps get more responses without seeing a dip in activities.
What your thoughts on talking?

Let's review the subject line: Poutine and ice storms

I'm not going to do this for every email, but I want to go over it for this example.

This subject line got an open because it is vague enough to draw an open and related to the body of the email to create context for the subject. Don't try a subject on your email unless it relates to what you are talking about. Notice I didn't make it "LeadIQ and Your company" or something generic and thoughtless. The other thing to keep in mind is preview text on a cold email needs to be about the prospect so they see it on the badge on their phone, should they open it there.

Now, how did I come up with this story? Well, see how you know the whole story from reading the cold email? That's how a cold email should be written. You should be able to print out your cold email and have your mom put it on the fridge right next to your terrible childhood macaroni art, and have anyone who reads it understand what you were saying in the email. Context is everything. The context is clear reading the cold email. That's so important when you are prospecting.

Email #2: Make the Prospect Feel Good

Okay, I'll admit. Sometimes you will look at a LinkedIn profile and get stuck because the prospect doesn't have too much information. This is usually the time to fall back on the company and what's going on with them, but other times you can be clever with your copy and use humor to get personal context.

Here are some tips on what to do when you cant find anything on your prospect online. 

This prospect had something their job description that said they were the operations person the company that connected all the tech together.

Here's the email that I sent:

"Subject: THE CONNECTOR!!!

Hey ****,
Was poking around on your LinkedIn and noticed that you mentioned you are the CONNECTOR... emphasis on the TORRR part (so it sounds cooler) at *****. Man I wish I could make the TOR part bigger in this email.
Anyways...since you connect up all the tech that your company uses in your stack, I was curious if you were ever looking for a way to connect LinkedIn Sales Nav to Salesforce for your reps, but with fully enriched contact data?
We help reps not wanna pull their hair out when they research a prospect by making it one click to create a new lead into Salesforce.
Does this seem like something “The Connector” would want to solve? What are your thoughts?

First things first, notice how I'm making the prospect sound badass without making fun of them here. That's a big part of writing cold email copy.

You want your prospect to feel good reading your email. I basically turned him into an SNL sketch called "The Connector." It's personalized enough where I didn't fake the personalization, and I even commented on how I wish I could make the font bigger in the email to make it seem like Phil Hartman is doing the voice-over.

My value prop is also customized for his role verse, so the specialization makes more sense relating to what I'm selling.

Email #3: Use Common Ground to Get a Conversation Started

I looked at this prospect's LinkedIn profile and saw that they started as an SDR out of college, similar to me.

Enterprise Sales Development Representative job description screenshot

I thought that'd be my angle for the cold email. Sometimes the easiest thing to do is find common ground with your prospect as quickly as possible.

Here's the email that I sent:

"Subject: SDRing in a past life....

Hey *****
I saw you used to be an SDR before you moved into your role two years ago. I’m actually used to be an SDR too before moving to marketing. It helps a ton having that skill with us for life.
Do you remember when you were an SDR how many steps it would take to reach out to someone? That's actually why I'm emailing you.
We could save your reps from the horribly long and gruesome process of having to create a new prospect in Salesforce before emailing or calling. What are your thoughts on talking?

Email #4: Knowing Someone's Connections and Past Companies is Useful

Sometimes mutual connections on LinkedIn and past companies can be enough personalized context to relate to someone with cold prospecting. Here are some more tips on how to prospect more effectively with LinkedIn. 

In this example, I knew this prospect worked with someone who was kind of cool and interesting, so I thought I'd ask if he knew him as the thing that made him special to me.

Again notice you understand the whole story by simply reading the email.

Here's the email that I sent: 

"Subject: Matt and your old company

Hey *****,
I noticed before you worked at ***** you worked at *****. Did you work with Matthew Epstein? Guy is sharp as a whip. I remember 10 years ago he made this video to try and get a job at Google. I guess it didn’t work, but it helped him get a job. Anyways, I wanted to see if you’d be up for talking?
We help make life way easier for sales teams when they are prospecting...so they can spend more time doing things that a bit more thoughtful like Matt did. Things like adding prospects from LI to Salesforce with full enriched contact data are only one click.
Does this seem like something that could help *****? What are your thoughts on talking more?

Email #5: Conversation is Important, Talk Like a Human Being

So for this one, I saw the prospect was connected to someone I knew, and I also saw their website and was blown away at the web design for it. Rather than being mum about it, I just opened up and went for it telling them my opinion.

Here's the email that I sent: 

"Subject: How do you know Scott Ingram?

Hey *******,
How do you know Scott Ingram? I did a talk at his conference in Austin last year. It opened up with a bunch of boos from the audience (it’s about prospecting tips...bug me for a link if you wanna see it).
I was curious if you’d be up for talking with me man? By the way, whoever is the web designer for ****...this effect is INSANE:
GIF of a website in action
We help reps with cutting down steps in their prospecting and making it easier for them to research their prospects off LinkedIn. Usually we can save them 6 hours a week
Does this seem interesting? What are your thoughts on talking?

Now I'm not saying you can ignore personalization, but you also could prospect a list of Scott Ingram's contacts that you know and still sneak in some personalization. You don't wanna get caught doing "fake personalization" because what happens if the prospect calls you back.

If this prospect called me and mentioned Scott Ingram and I blasted a ton of his connections, it'd be hard for me to remember who is calling me. If the person mentioned the web design email though, I'd know exactly what they are talking about.

Email #6: Share Your Own Story in Your Email

We need to be more vulnerable with our prospects. That means opening up with our insecurities, talking about goals, and explaining our why's when we prospect. Storytelling is important in sales. 

Here's the email that I sent: 

"Subject: You invented sales enablement

Hey ****,
I saw you are the head sales ops guys at *******. I'm actually working on doing some Sales Enablement here on the side while I work, but it's been kind of difficult.
You’re maybe one of the most experienced sales ops people I’ve ever come across. I was curious if you’d be up for talking with us?
We’re trying to solve the issue of cold emails and cold calls having the lowest response rates ever by making it more efficient for reps to research their prospects off LinkedIn and add records in the CRM.
Every bad unresearched prospecting email or call they do is teaching prospects to ignore cold calls and cold emails.
What are your thoughts on talking more and swapping some stories?

One of the easiest ways to do this is to tell them what you don't know. I tried to capture this prospect's interest by sharing my vulnerability. I see a lot of people say send "I need your help" emails. Rather than telling a prospect this, maybe you can show instead.

Email #7: Bring up an Influencer Your Prospect Follows

Under the "interests" section of LinkedIn, you can see different topics the prospect is interested in that you could potentially bring up in your outreach. This particular prospect I was looking at followed Tito Borht. Not only did I bring up Tito Borht in my outreach, but I also brought up some context about this prospect's old company since I had worked them before.

Interests section on LinkedIn

Here's the email that I sent: 

"Subject: Tito is the man

Hey ****,
I noticed on LI you follow Tito Borht. Did you ever see that study he did with all the different data providers with SalesHacker? Tito is the man.
He went through and had his company call a bunch of prospects using us, and a few other providers that help companies with prospecting data.
We met some of your old ******* team at SalesLoft’s conference a few years ago about doing some integration stuff. I was curious if your new team would want to check out LeadIQ for prospecting?
We help companies not just get data, but move data between LinkedIn and Salesforce. What are your thoughts on talking?
P.s. Did you apply for this new job before COVID or after?"

Email #8: Share Your Opinions in Things You Care About

This next prospect was someone that I saw who used to sell ad times at Adult Swim. I thought it'd be cool to talk about that and bring up my favorite Adult Swim shows.

Here's the email that I sent: 

"Subject: Selling at Adult Swim?

Hey ******,
I saw you used to work for Adult Swim? That’s crazy! What were you selling there? I used to love watching the Boondocks and Sea Lab 2021 when I was in high school.
I was looking at your LinkedIn and noticed that you managed the SDR team for a long time at ***. I was curious if you’d be up for talking? We make it so SDR’s don’t have to do needless data entry every time they want to prospect someone off LinkedIn.
For example, for you, all I had to do was hit one button you got pushed into Outreach and Salesforce with full contact data. Is this something you think your team would like to play around with?
I’d be cool hear some stories about your old selling days too. What are your thoughts on talking man?


So as you can see, you need context for prospecting. But you also need your own voice and personality put into the personalization as well. An email I write should be very different than an email you write.

If you came in here because you are searching for the best cold email templates, the harsh reality is this: Templates leave your cold emails to luck.

Get out there, start on LinkedIn, find context, and get writing. You'll not only like the challenge, but you'll also see an increase in response rates.

Posted by Ryan O'Hara
Ryan O'Hara
Ryan O'Hara has been an early employee at several startups helping them with marketing and prospecting tactics, including Dyn who was acquired by Oracle for $600+ million in 2016. He's had prospecting campaigns featured in Fortune, Mashable, and TheNextWeb. Ryan specializes in branding, business development, prospecting, and coaching people on how to make good digital first impressions. He also mentors two accelerators, The Iron Yard and The Alpha Loft, and hosts The Prospecting

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