By: Ryan O’Hara

One of my SDRs sent an entertaining cold email to generate opportunities.


As many of you know, while we’re getting the wheels turning on LeadIQ, we’re actively prospecting using our own product to build our company. We believe that the best way to know what our customers are going through is do what they do everyday; send cold emails. 

I don’t want to toot my own horn here, but I’m very good at email prospecting. I wasn’t good out of the gate though. It took me years to figure out what works, what doesn’t work, and how to prompt replies. When I first started email prospecting in 2008, it was still kind of a new idea for a lot of sales teams.

I am not a Bragasaurus Rex.

I’ve emailed influencers, helped a small company turn into a half billion valuation thanks in part to sending cold emails, and even had prospecting campaigns featured in the press. To be transparent, I’m mentioning this because I want to establish my ethos before I go into the events of last week.

There weren’t companies like LeadIQ, the Outreaches and the SalesLofts writing about email pitching. Luckily enough time has gone by to have data and many examples of techniques that work, and we’re learning more and more every day.

With that being said,  we hired our first full-time prospector, Jim Morris, a few months back. Jim is helping us in two major ways. First, building pipeline, and second, and more importantly, to prove out some of the concepts we talk about in this very blog. Jim works super close with me and Cole Fox.

Jim’s practicing all of the same prospecting techniques we discuss, but while he prospects, he’s also collecting data for us to write about. We’re running prospecting experiments and reporting them to you, so your team doesn’t have to.

Last week, Jim launched a really fun prospecting campaign that focused on using humor in an email, giving people a casual tone, and offering them something free. This was email he sent:

Jim’s email sent on Thursday night. The Subject: Your Bitter Rival

I’m really proud of Jim. This is a great email, and I’ll go into why shortly. He sent variations of this email to a number of Director of Sales from companies we specifically have been wanting to work with.

However, on Friday, Jim received a reply that was one of the most unexpected replies I’ve ever seen:


Yup..this email is real. I’ve blocked out their name to save them from absolute humiliation, and possibly being fired. 


Jim shouldn’t be discouraged. Let’s talk about why this Sales Director is wrong, and why Jim sent a great email.

Reason #1: Relationships are everything! We could have been your potential customer some day.

“Congratulations on being the douchiest sales guy of the year!!!! You might want to save your arm for jerkin’ yourself off instead of arm wrestling – an equal lack of true fulfillment for you I’m sure.”

You’re a sales rep. Every contact, every relationship you make, could be your next million dollar deal. I’d take 5 good relationships over 10 paying customers any day of the week, and so should your sales team.

Good relationships lead to many customers, as opposed to just one. 

There’s no way to spin it.

Jim’s email is great because it focuses on building relationships first. He uses humor, wit, and writes to the person like they are human being and not just some corporate entity.

Jim subtly brings up the product, but almost as a secondary subject of the email, and he compliments the prospect. He even relates to them saying they both do the same thing (which is completely true). This first email jumps them to Stage 2 of conversation; common interest.

Remember, Jim’s goal is to get a reply, and the best way to start a good relationship with someone is to have fun and be real with them.



Another prospect who received a similar email, though not interested, liked the approach, and will be easier to follow up within a few months. He or she may even recommend LeadIQ to someone. 

Reason #2: Jim got what he wanted most out of sending this cold email: a reply.

“Tip: if you want to sell to serious businessmen like me (& serious business women), then you should take yourself, your company, and your communication more seriously”

If you’re new at sales, never be disheartened by people like this. Jim’s goal with this email wasn’t to shoot off bullets about LeadIQ, or push a promo with boring typical sales language. Jim’s goal with this email was to get a reply to start a relationship. 

This Sales Director replied! It’s estimated it takes 6-8 touches with cold emails before you get a reply. Jim got one on the first try.

Think of it like this. I personally have better results writing personal follow-up vs. using an automated mail merge, so Jim’s naturally going to do the same thing.

So if Jim had to take the time to come up with 6-8 more ways to follow up personally, between realizing he had to do the follow up, checking his CRM, coming up with the email content, and sending it, each email could take as much as 5 minutes to write and send. Getting the reply just saved Jim 30-40 minutes, that he can spend on a prospect who potentially has interest.

I don’t subscribe to the whole “sales in a numbers game” methodology, but a lot of old school Sales Directors like this person who replied certainly do. Think of how many prospecting emails or cold calls you can make in 40 minutes?

This was a great email because he had a clear call-to-action, and ending with an open-ended question, which helps prompt email replies.

Some people can’t stand not answering questions, and not responding.


Why not show another response?


Reason #3: Good emails don’t waste real estate explaining who you are.

“Hey whoever you are…Jim? Do I know you? No! I don’t! WTFRU?!”

We’ve talked about this a lot on this blog. If there is any info about your company in email, it belongs in your email signature,  Jim’s email included the following info:

  • His name
  • A website link.
  • Links to LeadIQ’s social media
  • A LeadIQ explainer video
  • An event that’s in that person’s area.

In his email content, he gave one sentence about LeadIQ, and also told the prospect he is also a sales person.

  • Total character count about Jim and LeadIQ: 192
  • Total character count of the whole email: 901

Me/You Ratio: The ratio of the email used to be selfish 21.3%. Not bad Jim…not bad at all. 

Another one of Jim’s happy prospects who enjoyed the email agreed:



Jim shoots and scores!

Reason #4: 62% of Millennial don’t know what BTFOF means.

Good cold emails should be clear and concise. Being informal and casual is a great approach to seem more human, and remind your prospects that both you and he or she are not a machine.

Social selling is one of the ways to do this, collecting as much intel on a prospect as you can.

In the spirit of the reply Jim received, I surveyed over 30 Millenials and asked them:

Do you know what BTFO means?

Interesting enough, only 38% of those surveyed were familiar with the term.

When talking with prospects and others in your industry, it’s important to remember that not everyone is in on slang when being casual.

Luckily in Jim’s email, he was casual and fun enough to generate replies, get us new opportunities, and still avoid confusing people with his outreach.

Don’t get discouraged. Get replies!

Reason #5: Jim’s email stands out

Today alone, I got 108 emails, and over 16 of them were sales or marketing emails.

This was an email I got from this guys company after signing up as an anonymous lead.




I don’t care if you are targeting a Fortune 100 company or a small startup, standing out helps so much with cold prospecting.

That’s one of the big reasons we make copy interesting on our website, we write entertaining and fun emails, and give people an experience that typically stands out more than traditional prospecting. Sales people need to think of prospecting as cleverly as they would advertising.

First impressions should be thoughtful.

With these tactics, there are going to bumps along the way.  The days of the stale corporate sales culture, selling with an amputated soul are done. We have the data that proves this. We have users who tell us this every day.

Being casual, having fun, focusing on relationships first vs. the sale, being selfless with emails, and standing out is working.

We’re increasing our amount of opportunities, getting higher reply rates, and more deals while sending less email per day. This approach works. 

If you find yourself committing to these tactics and examples we share, please don’t let bad replies like this Sales Director’s get you down. They are going to happen, but you have to keep being yourself.

Always remember, any email you write could be posted online by someone. Ask yourself before you send an email, “Would I want my friends and family to see this?”

If that answer is no, you’re likely not writing a good email.

I’m not even talking about this reply being inappropriate either. I mean the email you write should be awesome enough to show people you know. It should be something you’re really proud of.

It’s needless to say, I’m really proud of Jim.

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Ryan O'Hara