How to Send Super Personalized Emails (That Prospects Actually Want to Read)

How to Send Super Personalized Emails (That Prospects Actually Want to Read)

When you send personalized emails to strangers, there’s something missing that you need to grow:


Many people skip this step, and it’s silly. It’s like keeping a plant boxed up and expecting it to grow anyways. You can’t jump right into asking for something and assume that custom fields like [Company Name] are enough to win strangers over.

Those tactics don’t build trust, and they don’t get the reply. So, let’s look at tactics that do.

From your email greeting to your closing — your message should be personalized from head to toe.

Below we look at six powerful ways to nail personalized emails, backed by psychology and real-world examples. Try them out and watch the trust (and your reply rates) grow.

mail-openPersonalization at scaleMulti-touch customized outreach right from your Outlook or Gmail inbox

1. Find an Uncommon Commonality

The quickest way to win someone over when writing personalized emails is to show how much you have in common.

That’s because we tend to trust those who are similar to us.

This psychological principle works even better when you emphasize something unusual you have in common with another person. Give and Take author Adam Grant does a great job explaining how this works:

“We bond when we share uncommon commonalities, which allow us to feel that we fit in and stand out at the same time. Think of the last time you traveled abroad and met someone from your hometown. If you met at home, the connection wouldn’t stand out as unique, but on foreign soil, you’re the only two people from there, so you feel a sense of closeness.”

How to Create Personalized Emails From Uncommon Commonalities

Check your prospect’s LinkedIn, Twitter, Google, and public Facebook profiles for shared backgrounds, hobbies, likes, dislikes, etc.

Do you have something in common that’s not particularly common? Mention it in your email.

Highlighting unusual similarities — especially in initial outreach — could be the leg up you need to get a reply from someone who might otherwise ignore you.

Let’s take a look.

personalized emails: personalize with similarities

Disclaimer: All emails are based on real emails but altered for anonymity.

2. Highlight Mutual Connections

Can we all agree that receiving advice from someone who can’t possibly relate to what you do is downright frustrating?

It’s a feeling that is all too familiar for anyone who has received a non-personalized B2B sales email. Here’s someone you don’t know, telling you what you need in order to do your job better.

Mentioning a mutual connection in the body of your email is one way to avoid this unfortunate scenario. Because when it comes to valuing the opinions of others, we take cues from people we already know and trust.

It also shows that you’ve done your research and you mean business — literally.

How to Personalize Your Emails Using Mutual Connections

Here’s a couple of ways to go about this in your personalized emails:

  1. Have your mutual connection send the email for you.
  2. Reference their colleagues or other decision-makers. This is great social proof that shows you’re being taken seriously by people they can relate to.

Here’s how a Yesware sales rep successfully used tactic #2. This email has a 33% reply rate.

personalized emails: personalize with connections

3. Send Your Email When It Is Most Likely to Get a Reply

We love sharing Yesware data and prescriptive advice on how to send more effective emails. And our findings are just that: A jumping-off point for you to test and iterate on what works best for you and your prospects.

So, when writing personalized emails, why not send them at a time that prospects are most likely in their inbox?

We’ve got you covered.

How to Send Your Personalized Emails at the Best Possible Time

In a recent Yesware 2020 study, we analyzed hundreds of thousands of email activity to dissect the optional timing for cold outreach based on reply rates.

Based on our data, the best time to send your emails is at 1 PM. And the second-best time is 11 AM.

best time to send email based on reply rates

This data tells us that 1 PM receives the highest replies, with an average of 46,000 replies. And 11 AM, the second-highest replied time, receives an average of 45,000 replies.

And based on the same data, we also dissected the best day to send your emails.

The data tells us that Monday and Tuesday are the most active time periods when replying to emails. Monday takes the lead by a small margin.

best time to send email based on reply rates

Connecting the dots: try Mondays at 1 PM and 11 AM & Tuesdays at 1 PM and 11 AM. See if you get a spike in replies, then work from there.

And remember, it’s all about what resonates with your specific audience. Use this data as a starting point for your own testing.

10 Cold Email Formulas That Just Plain WorkSee how B2B sales professionals are using these cold email templates to engage more prospects, fill the top of their funnel and build more sales pipeline faster.

4. Reference Specific Hiring Pain Points

Addressing someone’s specific pain points can be a powerfully effective way of writing personalized emails and earning their reply. That’s because pain motivates action even more than pleasure.

To find what’s keeping your prospect up at night, look no further than their company Careers page.

How to Create Personalized Emails From Open Job Postings

Check the open job listings on your prospect’s company’s website to see if they’re hiring anyone who would use your product. These postings will tell you:

  1. The pain points that have prompted the company to hire additional resources.
  2. The title of the hiring manager, who will most likely be the decision-maker you’re trying to reach.

Strike a chord by bringing up the issues that your prospect is experiencing, and then offer a more immediate solution than a new hire.

Here’s how one Yesware sales rep did just that (and got a reply).

personalized emails: personalize with hiring pain points

5. Use Their Name More Than Once

“Few things light us up quite like seeing our own names in print or on the screen,” explains Copyblogger.

Our name is tied to self-perception and our identity. Hearing it engages us. There’s actually science that backs this up.

How to Make Your Emails Look Hyper-Personalized Using Only Their Name

Use your prospect’s name in the subject line and body of your personalized emails.

Here’s an effective email that does just that, without going overboard.

Subject Line Tip: Here are 20 cold email subject lines that generate over 85% open rates.

personalized emails: personalize with name repetitiveness

6. Personalize With Praise 

Just like hearing our own name, receiving a compliment has a positive effect on our brain. It warms a cold email.

Use compliments in your personalized emails to create subconscious, positive attitudes toward you and your company. It works, even when a prospect recognizes it for what it is: a sales tactic.

Research shows that your prospect will still develop a positive attitude toward you.

How to Personalize Emails Using (Sincere) Praise

Check these places for news you can use:

  • LinkedIn → recent promotions
  • Google → funding announcements, product launches, or other announced achievements

Be specific in your email. Don’t just say, “I’m impressed by you.” Explain why. If you don’t point to a specific success, you risk getting sent to the trash bin with all the other generic emails.

Let’s take a look.

personalized emails: personalize with praise

mailSave top-performing emails as templatesNever write the same email twice with Yesware


With all the information we have at our fingertips to help us understand buyers and tools to help us be more personable – there should be no more generic and non-personalized sales outreach in 2020.

These six ways to send personalized emails plus hundreds of more accessible online should give you the leverage you need to start testing and measuring new techniques.

When you master the art of personalization, you’ll undoubtedly find yourself receiving more replies, having better conversations, and winning more deals.

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