5 Hacks to Cold Emailing Everybody needs to pitch, sometimes.

Cold Emailing Hacks

As every entrepreneur is a sales person, and everybody can benefit from the expertise of others, I decided to spend my last night in Boston (after 4 days at INBOUND17) at the “Rate My Pitch” meetup event. It was put on by the Boston Enterprise Sales Forum Meetup group at the LevelUp offices.

Ryan O’Hara (LeadIQ), Cindy Littlefield (The Bridge Group, Inc) and Carole Mahoney (Unbound Growth) rated our pitches and shared their knowledge. Here are my 5 key take-aways.


1. Do Your Research

What do you respond to most, a personalized note or the generic “I want to add you to my contacts” message? The personalized one, right? Well, so do your prospects.

Take the time to research your lead – but don’t overdo it, either. You don’t want to appear like you’ve been stalking them! As Cindy Littlefield pointed out, you do want to cover the 3 Cs:

  • Company
  • Contact
  • Conversation starter

Ryan O’Connor suggests taking 10 minutes to research the lead, find an angle, get contact info, write the email and send it. As you get better at cold-emailing, you’ll be able to reduce your research time to 5 minutes.


2. Be Short

Everything in your email should be short and concise.

  • The subject shouldn’t be much longer than 5 words.
  • The body of your email should consist of 3 paragraphs, ideally of 1 sentence each.

Your test to see if your email is short enough: send it to yourself and view it on your phone. If the subject line is not broken off and if you can read the entire email without scrolling, it passes the short-test.


3. Be Prospect-Centric

The person you are cold-emailing does not care about you, your company or your customers. They care about themselves, so put them first.

This is not to say that they never will care to know about your credentials, experience and great success stories, but these marketing elements come later in the sales process. In a cold-email, don’t write more than 1 sentence on yourself and/or your company.

Engage them first. Later, they will ask about you.


4. Be Trigger-Happy

Always have a trigger for the person you’re reaching out to. Share an article. Mention a mutual connection. Do something for them.

Just like journalists will only pick up a press release if there’s actually something NEW announced in it, people will interact with your email only if there’s a clear trigger that’s of interest to them (hence, the research).


5. Span It Out

Don’t try to do too much in 1 email. Sales is a process, and you can’t run a sales process in 1 email.

Break down your sales campaign into 4 stages or emails that you’ll try to span out over 1 to 2 weeks. Coupled with viewing their LinkedIn profile, sharing articles or liking theirs, these actions are touch-points. Don’t expect traction from your sales process before at least 5 to 9 touch points.



Remember, the goal of a cold-email is to start a relationship. It’s not to sign a deal or even to set a meeting. As Carole Mahoney pointed out, “Before you have a sales conversation, you have a human conversation.” This is my new sales mantra.


Photo by rawpixel.com on Unsplash

Leave a Reply

Your email address will not be published. Required fields are marked *