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Outbound Sales
  •   6 min read

How to Add Substance to Your Outbound Emails with Gabrielle "GB" Blackwell


ByNiharika Ayyagari

Published August 25, 2023

Outbound for Dummies Gabrielle GB Blackwell

Outbound sales is like taking a gamble. You reach out to prospects who may or may not have heard of your business in hopes of getting a response from them. 

Outbound emailing is usually the central part of your sales strategy. The question is - Can you increase the probability of a response? The trick lies in the content of your emails. You don’t want the emails to be spared of information, at the same time you don’t want to bloat the email copy with unnecessary content.

You need a good balance between personalization and relevancy, depending on the decision-makers and personas of your prospect list. 

To help us learn how to draft the perfect outbound email, Gabrielle “GB” Blackwell (Creator of The One on One, Sales Development Manager at Culture Amp and LinkedIn Top Voice) covers the topic “How to add substance to your outbound emails”, as a part of the second session in our ‘Outbound for Dummies’ series.

We started this series to simplify the outbound sales process which can get a tad difficult at times. With the help of expert leaders and managers in outbound, we cover the topics and questions that are always running on your mind. 

Below is an excerpt from Gabrielle “GB” Blackwell’s session. 

Leave No Crumbs During Your Groundwork 

You cannot compromise on research. Look at Salesforce, Google, their jobs page, and website - thread all the information together and see how you can string together some strategic narrative, align your value proposition, and then ask a question to start the conversation.

Here’s what to look for specifically: 

a. Before you reach out, make sure you’re prioritizing your book of business. 

b. Next, dig a little more and understand why this is a great account that should be prioritized.

Find answers to questions like - Are they growing? Did they just have layoffs? Are there specific areas in the business that they're investing more into? Are they trying to expand globally? 

c. Check if they have a job opening.  This will help you gauge what goals they’re trying to achieve or initiatives they plan on getting behind. 

d. Now, it’s time to identify where your company and solution fit in. How can you support them in what they're already trying to do?

Hot tip: If you can't find anything on the person, it might not be a great idea to go after them or the account. 

Spread your Sequences

It might take you two or three sequences before you actually get a response. That means that you don't need to shove everything down in your first outreach.

This is how you can divide your sequences: 
1. Your first cadence can be based on the account. 
2. Take a pause for 20 to 45 days. This time around, tailor the cadence to the person. 
3. In your third sequence, you can reach out to the person after you see something fun on their page, or if you stumbled upon their article, quote, etc. Draw them into a conversation based on that, and then bring up the problem. 

Hot tip: A/B test your CTAs. Don’t ask if they’re interested. Have a CTA along the lines of - How are you thinking about a common challenge that a lot of people are going to face?

Read: 30 sales sequences from companies like Hubspot, G2, etc. 

How to Find the Connection

Outbound prospecting is a field of educated guessing. Your company might already have a pre-existing connection with the prospect.

They could be following your company’s social channel, or they downloaded one of your content pieces a while back. It could also be someone who requested a demo in the past.

Check if there are people at your prospect accounts who have previously worked at companies that are current customers of yours.

And you never know - your prospect could be connected to one of your coworkers on LinkedIn. Reach out to your coworker, asking for an introduction. 

But if you still can’t seem to connect with the decision-maker - find out who closely works with them and ask them for a referral. 

Eg: “Hey, it's Gabrielle from Culture Amp. Listen, I know you are not the right person to talk to. I'm just wondering if you can help me out because I'm not trying to sell to you.” 

Read: How to ace outbound prospecting (5 killer tips)

Lengthy Vs Crisp Emails

The length of your emails does not matter. What matters is if you don't have anything of significance within them. 

You can't talk strategy with people who are below the line (tactical level). They might only think about how to eliminate all the manual and tireless activities. 

You want to make sure that you understand what value means at different levels of the organization. Build content based on whom you’re reaching out to, as relevancy plays a huge role in getting a response.

Cold Email Framework

Start with a little introduction. Tie in your relevance, and value statement (this should be attention-grabby), and then move to your launch question. As GB says, this is called ‘The Gamble.’

Make sure your first line is relevant to that person. Your value statement should make them realize why you’re reaching out to them. 

With the launch question in the end, make sure it’s easier for people to respond. What exactly do you want them to do? Never miss out on adding a CTA.

Read: Top 10 Cold Email Templates

How can Managers Enable Teams to Be Successful? 

Make sure you have a standard system of measurement. Recognize the themes and trends to keep in mind to evaluate email performance. List out any specific industry, messaging, personas, etc. your team must consider while building the sequence. 

Give your team a foundation for writing new sequences and emails. Build sequences together, and if they’re not working, figure out the whys and hows and alter them accordingly. 

Have team meetings to celebrate the big and small wins. Ask your reps to share what worked for them. This will help others get a fresh perspective and maybe next time they’ll try using a similar approach. 

Hot tip: Every Friday you can run a ‘email hot take’ hour. Here you can ask reps to submit their emails and then have everyone on the team pass feedback. This is how you can grow collectively, as a team. 

Some Secret Sauce(s) 

  • What people are not doing enough is leaving voicemails, and referring people to their emails. 
  • Have a bounty list of prospects - keep engaging with them, call them, and follow up constantly. And also store a general list of prospects, who you don’t really know much about, and put them in a sequence. 

    As a part of her bounty list, GB says she has a list of 200 phenomenal prospects. 
  • Personalize sequences for your high-priority prospects. Work their sequences for 30 days, and if you don't get a response, tell them you’ll reach out to them in 2 months. Most of the time, they’ll get back to you with future availability. They can now be a part of your bounty list. 
  • (We love this tip!) Ask Chat GPT to write an email based on the persona and style. Edit it and make it your own. Then feed the same email back to Chat GPT and ask it to evaluate the changes that were made. With the changes that the AI lists, you can keep those parameters in mind the next time you craft an email. 

If you want to listen to GB’s entire session recording, you can click on the video below. It’s everything you need to build your next outbound email up for success. Good luck out there! 

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