Outbound sales email

Automating Outbound Sales Emails Tips

A question my clients often ask is “How can I leverage automation tools to ramp up leads?” To answer this question, I usually suggest we need to first take a step back, focusing on who their best customer is and clarifying their value proposition. You can have a look at Janina Bernardo’s recent email that outlines the steps in crafting an engaging email script. In this post I’ll look at how to balance both automated and manual processes in leveraging your outbound sales emails.


I’ve sampled a number of tools for building out email lists for cold outbound sales emails. Typically, I’ll start with LinkedIn for prospecting. While it’s on the expensive side, Sales Navigator provides much greater granularity when it comes to prospecting leads. You can search by industry, company size, keyword, job title, geography, and more. Once I have a good list from Sales Navigator based on the buyer persona I’m going after, I’ll then use another chrome plugin like Sales QL or Get Prospect. Tools like this let me pull email addresses, phone numbers and other contact information, and port them to a CSV file.

Preparing Your List

You’ll want to make sure you clean up your contact list before sending out your outbound sales emails. For me this involves both manual and automated processes. I make sure the first name column I will be pulling from is cleaned up, removing any blanks, last names or alternate names. If I’m going to be pulling a company name into the email, I’ll make sure I’ve removed longer versions of the name including INC or CORP, so the email will flow more naturally.

Once those manual processes are completed, I’ll use an email address cleaning tool to identify email addresses likely to bounce. Recently I’ve been using Debounce. They note that 30% of emails go bad in just one year. If over 10% of your emails are bad, then less than 44% of your outbound sales emails will be delivered. A bulk email verification tool can eliminate any bad emails and lower the risk of having your email account flagged.

Getting Your Messaging Right

There’s no use ramping up sending outbound sales emails until you have clarified your messaging. Be sure you have a clear value proposition, list out benefits to your target customer, mention current users or other facts that provide credibility. Of course, you need to  make sure you get all this done in less than 125 words, according to Hubspot.  Consider building a quality check process using the 3 R’s, making sure you have the right message, to the right people, in the right format! In an introductory cold email, you want to think about how you can focus more on the prospective customer than yourself.


General “best practices” are to avoid sending outbound sales emails on Mondays and Fridays and send emails between 6am and 9 am when possible. Depending on your offering, and whether your sending to corporate or personal email accounts, you can explore lunch hour and weekend emailing in certain cases as well. Yesware, provides some alternate ideas, suggesting that 1 pm is a very good time to send, right when people return from lunch. While you may be tempted to make adjustments to sending times based on your open rates, know that the data set needed to make good strategic decisions should be in the thousands of emails sent. In most cases its best to stick to industry guidelines.

Follow up

This step is where manual processes need to be engaged. A number of sales triggers can be flagged once outbound sales emails go out. If you get a direct response, hooray, you’ll need to decide to follow up with a personalized email or phone call. Other sales triggers that can automate a next step for you include click throughs and multiple opens. If you’ve sent 100 emails and have time to make 10 personal follow-ups, its best to start with the 10 people that show signs that they’re interested in talking to you. Outbound sales email tools like Mailshake creates a “lead catcher” that will help you automatically flag contacts that have fulfilled certain conditions and remove them from the automated sequence of emails. The last thing you want is to have a great sales call with someone, and then they receive an automated email the next day because you didn’t remove them from your email list. With some tools, this may need to be done manually…don’t forget!

Further Training

A few resources I recommend for further training on the topic of email automation, workflows, and building great outbound sales emails are:

MailShake Cold Email MasterClass: On the cold email side, the classes cover everything from subject lines, to quality check processes to how to write follow up emails.

Hubspot Academy: These free resources cover many topics outside the scope of this article, but in particular you, might be interested in Hubspot’s training around automated workflow, email templates and sequences.

VA Partners: Venture Accelerator Partners also offers direct training for startups and sales teams. Ontario residents may be able to leverage the Canada Ontario Job Grant which provides a grant covering 83% of training costs.  

If you are interested in connecting to discuss your own channel sales challenges email me: [email protected] or connect with me on LinkedIn.

Automating Outbound Sales Emails Tips