In the 1980s, there was a sitcom called "Small Wonder" in which a family tried to pass a robot-in-a-dress off as their 10-year-old daughter. (A shaky premise to be sure, but it was the '80s, so the show was a big hit.)

The one thing the show's robot daughter -- Vicki -- couldn't quite master was the way humans talk to each other. She was completely unnatural, saying things like, "Hello to family" instead of "Hi, Mom and Dad." 

These days, when I go through the inevitable pile of sales outreach emails in my inbox, I'm reminded of Vicki. Actually, I'm reminded of hundreds of Vickies, grown into adult robots and employed as sales representatives all across the globe.

It's not that they make no attempt at personalization -- it's that the personalization they attempt feels forced, a canned approximation of the sense of familiarity they desire. I don't need to dwell on bad outreach emails today. My sense is you've all seen an overtly templated email before. Instead, let's focus on the good ones.

The sales prospecting emails that successfully break the mold are those that reflect actual human curiosity, emotion and humor. Here are a few examples from my inbox today.

Three Great Sales Emails (And Why They're So Good)

1) Do Research -- Don't Just Scan and Paste

Somewhere along the line, we learned that a touch of personalization does wonders for getting prospects to respond to emails. Personalization has to be executed well, however -- it's more than just inserting your prospect's name into the subject line. Personalization that feels forced or shallow can have the inverse effect. All too often, I get emails from sales reps who clearly Google News-searched HubSpot and pasted a headline into a semi-coherent compliment.

This email from Monther Einajjar, Director of Business Development at was different. Monther did his research. And that research involved more than a quick scan of a news release on the company. Let's take a look.

HubSpot CRM & Localization

Hi Meghan,

I came across this article about HubSpot named as the winner of the 2016 CRM Watchlist. Congrats on that! 130 companies were evaluted so it's quite impressive that HubSpot was chosen.

How does HubSpot currently support its software and web content in foreign languages?

We are a translation services provider and we work heavily with companies in the computer software space. Our technology platform helps streamline our clients' translation process, reduce their turn-around time, and can connect with any content management system.

As we enter the 2nd quarter of 2016, are you available for a 15-minute introductory call sometime in April? My goal is to see if there is a fit between our two organizations and if we can support you in your future initiatives.

Hope to hear from you soon!

Monther Elnajjar, Director of Business Development,


Why it worked: Monther didn't just choose any random award from our history. He highlighted a recent accolade we're particularly proud of: Winning the 2016 CRM Watchlist Award for our free CRM. Furthermore, he looked into the number of companies we'd been up against for the award and pivoted that into a logical pitch for translation services for that same software. The personalization was relevant, well-researched, and fit nicely with his ask.

2) Design Your First Line For One Person Only

This series of emails from Evan Walker of FortyOak is among the best I've ever received. FortyOak is a headhunting firm that specializes in finding placements for technical marketers. So when he reached out to me -- a Marketing VP at a tech company -- he was already on solid ground. What made these emails so successful, however, is the care he took to craft the first line of each. Here's the first one:

Quick Intro | Evan <> Meghan

Hi Meghan,

I'm using your own technology to prospect you right now, so I guess that is kinda a compliment.

For context, FortyOak - FortyOak is a venture-backed strategic headhunting firm focused exclusively on performance based Marketing Technologists with a strong proficiency in Demand/Lead Gen & Growth Marketing tactics leveraging platforms such as: Marketo, Pardot, HubSpot, & ExactTarget.

Here is a profile of a candidate that I feel aligns with the role: <link redacted>

I'm also sending this sequence to Rebecca and Kipp so I look forward to hearing from one or all of you.




Why it worked: In the first line, Evan refers to the Prospects tool within HubSpot's free CRM. That's an immediate 100 points. He doesn't just know the software we make, he uses it. His use of our software is a clear indication to me that he knows our company well -- something that is critical for a recruiter to demonstrate.

Now, our CRM is free and built for sales reps, so understandably, you won't be able to do this for every prospect, but try to find your version of this opening line for every company you reach out to. If you can't try their product, reference an article written by the company or an employee you admire. Doing so right upfront will catch the recipient's attention, assures them that the information to follow is in context, and gets buyers to respond to emails.

3) Follow-Up Emails Should Inspire Intrigue, Not Guilt

I don't mind receiving outreach emails. I admire the strength and creativity it takes to try to pitch someone your business. What I can't stand are follow-up emails designed to provoke guilt or feelings of obligation.

Like many prospects, I get so many sales emails that it'd be a part-time job just to field them all. Occasionally I'll respond to the best ones (or, in this case, write a post about them) but I just can't responsibly afford to spend time on every message.

I think sales reps understand that. Which is why I can't understand why so many follow-up emails start with phrases like: "This is my third attempt to reach you" or "Just making sure you haven't forgotten about me." They induce a feeling I can only describe as "guilt-rage."

Like most people, I have a mile-long to-do list, members of my team I want to be spending more time with, and a puppy that looks at me with large pleading puppy eyes every time I pick up my laptop on a weekend instead of his squeak toy. There's enough in the world to feel guilty about without needing to add follow-up emails to inquiries I never requested in the first place.

All of which is why this follow-up email from FortyOak's Evan Walker was such a welcomed approach. After his first thoughtful outreach, I had been considering forwarding the candidate he'd passed along to one of HubSpot's hiring managers. This follow-up email effectively nudged me to do so.

Re: Quick Intro | Evan <> Meghan

Hi Meghan,

I got another landing page for the prospect button, however I used Twitter and learned we shared a hobby - SECOND LUNCH!!!

Take a look at this candidate: <link redacted> -- thoughts here?

I can also be reached any time on (XXX) XXX-XXXX.




This time Evan is referencing a tweet I'd personally posted that week.

(Don't judge, I was hungry).

Why it worked: I'll almost always put time into someone who has clearly put time into me. Not only did Evan demonstrate that he knows our software and business well enough to find a good-fit candidate for us right off the bat, he went the extra step in a follow-up email to demonstrate that he gets my sense of humor. Referencing a recent tweet is a surefire way to establish personal rapport without crossing the line into being too invasive. He also managed to avoid invoking my guilt-rage by keeping the tone light and not calling me out for my previous lack of response.

Find the Happy Medium Between the Template and The Personal

Each of these emails worked because they struck a chord with me personally. I know and respect how many emails and phone calls sales reps have to make on a daily basis. I can understand how hard it would be to craft a personal approach to every one. But so many templated emails could be improved by a single introductory line that demonstrates a touch of insight into the recipient. It's amazing what a thoughtful personalization of the first line will do for an email's success rate.

What emails have you sent or received that achieved this balance? What do you strive for in creating the perfect outreach email?

HubSpot CRM

HubSpot CRM

Originally published May 2, 2016 8:30:00 AM, updated July 28 2017


Email Prospecting