Email Prospecting Tips From A Former Spammer

Keith Carlson
6 min readOct 17, 2016

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Just like in real life, on the Internet, there’s more than one type of SPAM

I started my career on the Internet in the late 90’s as an email marketer. Anyone who knows anything about the history of the Web knows that, in the 90’s, “email marketing” was a euphemism for “spamming.”

Please don’t hold that against me. I was young, I was naive, and, unfortunately, SPAM was what you did on the Internet back then to make money if you weren’t a venture-backed company with millions of dollars to blow on Super Bowl commercials.

Oh wait… those companies didn’t actually make money.

Anyway, fast forward a couple decades, I manage the sales development team at a tech company, and we’re responsible for prospecting customers using cold emails, which means I’m still doing the same exact thing.

Yup… for some reason if you send cold emails offering strangers a pill that’ll give them a better sex life, you’re on par with the antichrist; but if you send cold emails offering strangers yet another SaaS accounting platform, you’re on the cutting edge of marketing. Go figure.

Luckily, two decades of experience spamming… errr… “cold prospecting” people has taught me plenty of tricks about how to get people reading and responding to my unsolicited emails. Here are some of my favorites:

Tip 1: Don’t capitalize anything in the subject line

Your high school English teacher would probably be pissed, but B2B, SaaS prospecting emails with subject lines that don’t have any capitalization get opened 28% more than subject lines with proper capitalization. For the record, this was also true back in my spammer days, but the open rate increase was closer to 40%.

Also, the worst thing you can do in your subject line is include all-caps words, like FREE TRIAL. Open rates go down by a whopping 64%!

Tip 2: A picture really is worth a thousand words

Short emails (100 words or less) get a 46% higher response rate than medium-length emails (100–500 words), and an 82% higher response rate than long emails. So, how do you say a lot with as few words as possible?

Add a picture!

Interestingly, short emails with images improve the response rate another 22%. More interestingly, the picture itself doesn’t seem to matter (within limits of not being offensive, obviously). Since product images are no better than including funny memes or GIFs, I tend to use the latter.

BTW — I like Quickmeme to create memes, and Giphy for GIFs.

Tip 3: Emails sent on Saturdays get better open rates, but lower response rates

Emails sent on Saturdays get better open rates because there’s not as much competition for attention. But the response rate — that is, the number of replies compared with the number of opens — goes down.

This trend is true for both consumer marketed SPAM and for SaaS sales, but I don’t know why the emails are less effective on weekends. My best guess is that people are more likely to flag emails as something to respond to later and then forget.

You might be tempted to send emails during the week to get a higher response rate, but my team has learned to value high open rates. The next tip explains why.

Tip 4: Recipients who opened your first email are 64% more likely to respond to subsequent emails

In an absolute sense, even the best response rates to cold email campaigns (5%-ish) are still quite small. So a minimal improvement in response rate on emails sent during the week isn’t as important as getting a higher open rate by sending emails on weekends because you can always send more emails.

In other words, don’t expect to get a response by sending just one email. Send a series of emails while paying close attention to the people who opened your first email since they’re more likely to respond to your follow-up emails.

You’ll need some sort of email open tracking software to get this info. My team uses RocketBolt because it’s free and works with Gmail. There are similar tools for other mail platforms.

Tip 5: Use “Fwd:” at the beginning of an email subject line

Back during my spamming days, adding “Re:” at the beginning of a subject line worked great.

We tried this with our B2B prospecting emails, and response rates went down. We even saw an increase in angry emails. However, for B2B emails, using “Fwd:” increased open rates 19%.

Specifically, the tactic is most effective as part of a follow-up email. You can basically just forward your original email and add a short note to it along the lines of “Checking to see if you saw the email I sent last week (forwarded below).”

Tip 6: Send the email from “Matt”

Everyone knows someone named Matt. Use this to your advantage by sending emails as though they’re coming from someone at your company named Matt. Note, specifically, the absence of any last name.

The email will appear in the recipient’s inbox as being sent by “Matt,” and your open rates will increase because recipients will think your message is from a Matt they already know. This technique increased open rates by 17%, followed closely by Dave at 15%, and Heather at 14%.

Note that this tactic is great for B2B sales if your SDRs are just teeing up phone calls for someone else. If the SDRs themselves are getting on the phone, the “Matt” tactic is going to be harder to execute.

Tip 7: Use a serif font

Font choice is probably one of those things you never thought about, but it can make a big difference.

For us, using a serif font like Georgia makes a difference to the tune of an 11% increase in response rates.

Why does a serif font matter? I don’t know for sure, but I think the visual difference it creates somehow adds to a sense that an email is personalized.

Tip 8: Include a call back number with an area code from the recipient’s location

This is a subtle trick my team is actually still testing, but early results are good. In our cold prospecting emails, we’ll include something along the lines of “… or feel free to call me on my cell anytime at…”, and then include a VOIP number with an area code tied to the recipient’s location.

No one ever actually calls the phone numbers (though we do have them properly routed in case they do). Instead, including a number with a local area code implies that we’re local, and people are more likely to work with local companies.

For phone numbers and routing, we’re currently using Call Fire. It’s a little pricey, but it seems to do what we need.

Tip 9: Add a link to your website in the first line of the email

Always, always, always include a link to your website in the first line of the email. People can’t help but click on that link. In fact, 78% of the people who actually open our emails click on the link to our website.

This is fantastic because, even if the person doesn’t respond, you can still retarget them using Facebook and Google ads.

Tip 10: Create subdomains for outbound prospecting emails

I don’t care what industry you’re in, if you’re going to send cold emails, you’re going to risk damaging the reputation of your domain.

To combat that, have your tech team spin up a subdomain for all outbound prospecting emails. For example, if everyone at your company normally uses an email address ending with “@example.com”, create the subdomain “@team.example.com” and send emails from there. Or, if you’re really paranoid, buy “@exampleapp.com” or “@tryexample.com” or some other variation of your company’s primary domain name.

The point is, even if it’s common practice, cold emailing is risky business. All it takes is a few people hitting the “Flag as SPAM” button to send your deliverability rates plummeting. That’s a single point of failure you don’t want to risk.

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Keith Carlson

Director of Marketing, amateur improv artist, extremely amateur karaoke artist