When you start personalized emails to strangers, there’s something that’s 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.

Below are six powerful ways to personalize your next email, backed by pyschology. Try them out and watch the trust (and your reply rates) grow.

Don’t just send personalized emails — see when they’re opened.

1. Find an uncommon commonality

The quickest way to win someone over 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:

personalized emails how to find a commonality

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. Here’s a look at how Yesware sales rep Cam Smith incorporated this personalization technique to win over a fellow BYU alum:

personalized emails_outreach example

Here’s the response that he received:

personalized emails_reply example

Set yourself up for success: The Ultimate Guide to Sales Email (Backed By Data)

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 an unpersonalized B2B sales email. Here’s someone they don’t know, telling them what they need in order to do their 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

There’s a couple ways to go about this:

  1. Have your mutual connection send the email for you. Sign up for a tool like Conspire that analyzes your contact list to identify acquaintances who can introduce you to the person you want to reach.

  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 Yesware sales rep Paul Hlatky has successfully used tactic #2. This email has a 33% reply rate.

personalized emails mentioning mutual connection

3. Send your email when it is most likely to be opened

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.

Your customers might be early morning mobile readers, or they might respond faster if you email them on a Friday afternoon. So, why not send your personalized emails at a specific time that will have the most impact?

How to personalize emails according to your prospect’s schedule

At Yesware, we’re able to pinpoint the best times to send through the Yesware Email Open Activity report in Salesforce. It shows us when prospects are actually opening the emails our sales team sends them, drawn from all the email activity and engagement data that has been automatically synced into Salesforce.

Our take-away: Tuesday afternoons are the best times to send emails to our prospects. As you can see in the graph below, that’s when opens are at their highest.

personalized emails when to send

If you’re not using Salesforce, you could also A/B test sending your email at various times to find the best time to send. What matters most is that you’re using data to inform your strategy.

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).

overlooked source for writing personalized emails

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

You can use your prospect’s name in the subject line and body of your personalized emails. Here’s a real email that I received and replied to (with rep’s name and company replaced for anonymity):

how to write personalized emails

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 of 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 being sent to the trash bin with other generic emails.

For example, here’s how Yesware sales rep Walter Bridglal cited workforce expansion specifics to personalize his congratulatory email to a prospect. That call he requested? Booked.

personalized emails that include a compliment

Pro Tip: Send Personalized Mass Emails At Once With This Free Template

It can be time consuming to find and reference personalized details about each prospect on your list, for every email you send. So we created a super simple template in Excel that you can use to organize all your research. It also allows you to quickly insert personalized messaging into every cold email—at one time.[the_ad id=”10333″]

If you happen to send drip or mass email campaigns to multiple people, you can use Yesware to send these customized messages. Save the template as a .CSV file and then upload into Campaigns to set up your mailing list and insert custom fields into the body of your email.

send personalized emails with yesware mail merge for free


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