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  • Gray-Winsler

How to personalize outbound emails so people actually reply

Recently, we asked our customers which lead gen strategies worked best for them through COVID-19. Of the 203 respondents, 38% said outbound sales worked best when compared to inbound marketing, paid digital / social advertising, and webinars / digital events. That is a huge chunk of respondents and a strong indicator that if you’re not already working on an outbound team, you should be.

With prospects more available at home, more willing to connect during isolation, and perhaps less likely to actively seek solutions to their problems, now is the time to be proactively reaching out to people directly.

There are many components that make up a successful outbound effort, but one of the most basic and fundamental building blocks are cold emails. Cold emails are critical because in many cases the email you send to a prospect is going to be that person’s first interaction with your company. Your job is to make them excited to reply. With 290 billion emails being sent and received each day, it’s no small feat.

Below I outline five steps toward writing a successful cold email that help start meaningful conversations.

Step 1: Write a captivating subject line.

What you write in your email only matters if people read it. So, your first goal is getting them to open your email. Subject lines should accomplish three things: 

  1. They should spark someone’s curiosity just enough to open the email. 
  2. They should hint at what the email will be about.
  3. They should stand out from other subject lines in a person’s inbox. These may seem obvious, but hitting all three can be a challenge.

The most common subject line I saw used was “{{company_name}} + My Company”. However, unless the name of your company describes exactly what your email is about, the recipient has no way of knowing what’s inside. So, unless they’re bored or compulsive, they have no reason to open it. It also fails the third test because it’s so over-used, prospects probably receive at least one email a day with this subject line.

If you read five blogs and they all say you should be including emojis, using a buzzword like “free”, or starting your first email with Re:, don’t do that. These might not be bad ideas by themselves, but if the advice is common enough, they’ll most likely be overused and end up losing any value they might have had.

Because of this, I can’t give you any copy-and-paste ideas, but I can give a few guidelines for your subject lines:

  1. Standard open rates for cold emails range between 15-25%. That said, the main subject line I’ve been using has hovered around a 60% open rate with over 200 emails sent in total, and I’m sure there’s still room for improvement.
  2. Vary the length of your subject lines to see what works. The first subject line I found that consistently hit 70% open was just two words long (“{{company_name}}’s proposals”). For reference, research suggests around 41 characters is the optimal length
  3. Write the body of your email first. It’s easier to write a captivating subject line once you know what your email is actually about. It also helps you avoid misleading subject lines that may have high open rates, but don’t actually relate to your pitch.
  4. Always A/B test at least two subject lines at the same time.
  5. Avoid any common tropes you see frequently used — this will help you stand out in a person’s inbox.

Remember, most of your work is going into the body of your email. Even if you get an 80% open rate, that means 20% of your work will be wasted. So experiment with your subject lines relentlessly and drive that number as close to 100% as you can.

Step 2: Prove you are a human.

The world is filled with spammers. Thanks to data aggregation tools, the information of any persona you can imagine is available. All you need is an internet connection and $100. That means any decision maker’s inbox you might be reaching out to is likely a nightmare, overflowing with robotic email templates sent out en masse to anyone with a pulse.

Because of this, the first thing you should do when reaching out to someone is prove that you are, in fact, a human. Luckily, if you are a human, this shouldn’t be too difficult.

What it comes down to is personalization. Generally, most of the information you want can be found on their LinkedIn profile or on their website. What you’re looking for is anything remarkable to comment on. Here are a few things you can look for to personalize your emails:

  • A recent blog post they wrote
  • A shared alma mater
  • Recent awards, recognition, or press (e.g. Series A raise)
  • Hobbies shared publicly on LinkedIn
  • Local events and news
  • A shared LinkedIn connection
  • A shared or high-profile customer of theirs
  • Name drop their colleagues — especially those whose success they’re responsible for
  • Reviews from their customers.
  • How long they’ve been in their role
  • Who their competitors are
  • What you love about what they do

Using videos within emails is also an easy, fast, and effective way to start a conversation. The highest performing template I’ve created so far (75% open, 11% reply rate) included no text at all — just a GIF linking to a 1 minute video. 

I believe this is because with video, even if you’re reading from the same script in each video, the added elements of tone and body language make it feel much more human and personalized. Video also forces you to say your pitch out loud, which helps to avoid any clunky wording.

The downside to using video exclusively is that it’s not skimmable. Unless someone views the video (and many won’t), they’ll know nothing about what you do or the problem you solve.

Step 3: See if they actually have a problem.

You have an awesome product / service, and if you’re like me, you’re probably excited to talk about how awesome it is. However, just because you have a truly awesome, life-saving solution, that doesn’t mean the person you’re reaching out to actually has a need for that solution.

Far too often, people launch into their pitch before prodding a possible pain point. This is a misstep. Before you pitch, you have to give people a reason to care about your pitch. The best way to do this is by highlighting a struggle you think they’re experiencing. Here’s an example email from Gorgias that does a good job at leading with the problem:

A solution is meaningless unless there is a problem. Lead with the problem they’re facing, and then give them the pitch.

Step 4: Give them a reason to reply.

Now it’s time for the pitch. This is where you communicate in the most concise way possible what you do, and how you can benefit your target company.

I generally find a good pitch includes two components: an emotion, and a number. For example, “Qwilr allows you to create beautiful proposals you will be proud to share 33% faster.” This way you’re talking to both the head and the heart, so to speak. This is also a good place to leverage social proof and highlight a customer that’s similar to your target company by sharing a case study.

If you’re lucky enough to have a strong customer base and a marketing team that conducts surveys, let that data inform your pitch. Look at what your customers love about your solution, and the critical pain points they came in with, and lead with that.

Just as with the subject lines, A/B testing here is critical so you know which positioning works best.

Step 5: Call to Action

I think pretty much everyone is familiar with what a good CTA looks like, so I won’t spend too much time here. With outbound, you’re typically asking for a call or for a referral — someone else at your target company that would be best to connect with.

The general rule here is to make it as easy for people as possible, which is why it’s good practice to include a direct link to your calendar.

Wrapping up

Okay, so what does all of this look like together? Here’s an example email from Gusto that does a good job at personalizing, poking a possible pain point, and giving a nice one-two punch reason to chat further:

If this email style isn’t your flavor, you can check out [Good Sales Emails](Good Sales Emails) for a heap of other examples you may find inspirational.

One thing to remember is that despite this article being relatively verbose, your email shouldn’t be. Each of the steps I’ve outlined here should be 1-2 sentences long. There’s a good chance you email is going to be skimmed, and short emails make it easy for folks to get the most important information at a quick glance.

Remember: Your goal is to start a meaningful conversation here, not spam 1000 leads and pray for a 2% reply rate. If you do your research, prod at the right pain points, and give people a concise reason to talk further, you will get replies.

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