How to perfect your sales emails and close more deals

Collin Stewart, CEO

19 December 2018

The more things change, the more they stay the same. 

The constant evolution of outbound sales has been an exhilarating ride: new and creative ways of reaching out to prospects are devised each day and more granular data is analyzed in the pursuit of better segmentation. There have never been more tools in the sales development toolbox.
Despite that evolution – brilliant as it has been – email remains the foundation of outbound sales. We’ve added so much nuance to our outreach, but it’s built on the strength, and effectiveness, of a well-crafted email.

Our co-CEO, Collin Stewart, discussed the importance of sales emails with a few other outbound heavy hitters – Steli Efti, CEO of Close.io, Don Erwin, Head of Revenue at Mixmax, and Dustin Crawford, Sales Manager at Intercom – during a recent webinar dubbed “How to perfect your sales emails and close more deals.”

Their wide-ranging chat covered the ins and outs of cold emailing; from ensuring you’ve nailed your niche, to designing an effective and personal email cadence, to incorporating humor in your follow-ups, this webinar was truly Sales Email 101.

The foundation: sending the right message to the right people

Sounds obvious, doesn’t it?

We talk about it all the time, and Aaron has devoted entire sections of his books to the idea that you must know who your audience is, and how to talk to them. Yet zeroing in on the right prospects remains a challenge for a lot of outbound teams (and companies hoping to establish outbound teams).

“Sales leadership, founders, and CEOs have an issue with saying “here is what we sell, go sell it” to their sales teams. I think this is a real problem,” said Collin, during the webinar.

“From your senior management, you need to be given the top 100 accounts, the next 1,000 accounts, and the bottom tier as well. Then, no matter what you do after that, no matter how many blog posts you read, or webinars you attend, it doesn’t matter. You have to send the right messages to the right people.”

Steli Efti, CEO of Close.io, agreed on this foundational principle.

“Sending the best thing to the wrong people will not convert. You have to know the account, know the person, have good data, and reach out. If 80% of the people you are reaching out to will never buy your product, you won’t get very far. No email subject line hack will overcome that,” says Efti.

“The fundamentals have to be in place – you need to know who your customer is, and who you are reaching out to.”

Crafting effective email copy

Let’s say you know your audience, your product is in the market and helping people, and you’re ready for the kind of incremental growth that only outbound sales can bring.

If that is the case, then it’s time to writing outbound emails. But, like all things worth doing, that can be a tricky proposition, with myriad elements to consider when putting your cadence together.

Do you send an email first? If so, how personalized should it be? Or, does a phone call make more sense?

“I’m a fan of sending the email first. If you know who you are talking to, and can send at scale, the email gives you context for a follow-up phone call as well,” says Don Erwin, Head of Revenue at Mixmax.

“But when sending the first email to a group of people, take some time, do some research, and make that email outreach as personal as you can. It shows you have done your homework, and will build credibility.”

Personalization is easy to say, of course, but much harder to do. And if you aren’t used to crafting tight email copy, figuring out where to add personal touches can be a challenge.

One simple way is to add the name of your prospect in the subject line, an element most prospecting platforms provide. A more nuanced method of personalizing emails, however, is to uncover the technology they use in their day to day and educate them on how you can help.

“Everyone says we work with so and so company, and we helped them do x, y, and z. But it is way more effective to understand the technology they are using, and the pain they are feeling. That leads to real conversations,” says Dustin Crawford, Sales Manager at Intercom.

“And if you tie that to a champion in the organization, that is very powerful.”

Finally, each vertical brings with it a unique vernacular – a certain set of terms that industry professionals use. Learning that language and incorporating it into your emails will help you connect with your prospects.

“My favorite place to start: An old mentor once told me to stop selling and just go visit customers to watch what they do, and write down how they talk about a product. He wanted me to get the terminology right when I was speaking with them,” says Collin.

“It’s tough when you’re selling software – everyone wants to talk about features, but no one cares. They want to hear about what the technology can achieve. That is what will resonate. That is what will make an impact. And, with email, you need to catch their attention quickly. So, how do you quickly get someone’s attention? Speaking in their language will go a long way.”

(Editor’s note: we spoke with email specialist Laura Lopuch a while back about how to write tight, engaging emails. You can read about it here, or listen to the whole podcast here.) 

The fine points: formatting

Once you have your list ready and your email copy is done, the last element to consider is what it will look like on a computer screen, and on a phone (don’t forget about the phone!).

It’s easy to get carried away with email copy, entrepreneurs love sharing everything they can about their companies, but in the world of outbound emails shorter is better. So, make sure you are also evaluating what your email looks like. If it looks overwhelming, start cutting.

“Whatever the length of your email is, if it is longer than a few sentences your prospects are likely not going to read it. The easiest way to get your email deleted is to send a full page report, unformatted. Remember they don’t know you, and they are trying to figure out what to do with your message, all in a few seconds,” says Efti.

“That tells your prospects you don’t respect their time and, if they feel that way, a partnership will never work out. Keep your messages short because you don’t deserve a lot of their time in the beginning. You have to earn it.”

For more cold email best practices – including how to incorporate humor in your copy, how to sell services effectively, and how to incorporate chat technology – check out the rest of the group’s in-depth discussion on The Predictable Revenue Pod.

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