In the age of sales acceleration and sales automation, it can be tempting to cut corners and scale at all costs. The more emails sent, the better, right? Not really. After all, what good is speed without quality, or efficiency without effectiveness? In this presentation, as asked some of the top sales development leaders to dissect some real cold emails so we can be more effective at sending good cold emails. Download the full ebook at Engagio.com/crappy-email-ebook

1. How to Not Send
Really Crappy Cold Emails
Brandon Redlinger Max Altschuler

2. How to Not Send
Really Crappy Cold Emails
Engagio.com/crappy-email-ebook

3. In the age of sales acceleration and automation, it can be easy to want to
cut corners and scale at all costs. But what good is speed without quality, or
efficiency without effectiveness. If you can send 100 emails to make one
connection in the same time it takes to send one email and make one
connection, who really wins? Companies should 100% invest in sales
technology, but they must also invest in hiring, onboarding and training
their teams to connect with human beings in a way that will get results.
There’s always going to be a fine balance between quality and quantity.
Introduction

4. The Modern Sales Mantra
It’s all about the right person, at the right
time, with the right message.

5. The purpose of this ebook is to give you a better understanding of how
to connect with prospects on a human level over email. We’ve taken
real cold emails from real reps and asked some of the best practitioners
to critique them, all in the name of helping you become more effective.
The book wraps up with actionable and functional best practices. Like
all good advice, the tips are given in the context of actual emails sent to
real executives.
The Purpose

6. Meet Our Judges
Ralph Barsi Heather Morgan Ray Carroll Trish Bertuzzi David Dulany
Josh HillSteven Broudy Phill Keene Blake Harber Richard Harris
Nicolette
Mullinex
Liz CainJake Dunlap
Brandon
Redlinger

7. This eBooks is a fun exercise to take entertainingly crappy emails and
critique what’s wrong with them. A lot of these emails are bad because
the person rushed or failed to personalize them. Shame on them.
However, we’re not here to make fun of or humiliate anyone, so all
names, emails, and companies have been redacted.
These are all 100% real and undoctored emails sent directly to us from
English speaking sales people in the USA.
Disclaimer

9. How to Not Send
Really Crappy Cold Emails
Engagio.com/crappy-email-ebook
Get the full, unabridged version
with full critiques now.

10. Crappy Email #1
The subject line is lame and generic. The intro is
self-focused, dull jargon. It’s too long.
When writing emails, think in terms of texts & tweets.
Write short sentences and paragraphs.
This is a classic shot in the dark. Is this even relevant to
the target? If not, don’t risk ruining your reputation.
Be specific in your CTA. “Do you have 10 minutes to
talk on Friday?”
Avoid yes or no questions, and be more clear in your
ask. Why should your contact care to get on the phone?

11. Crappy Email #2
Are you really interested in learning more about each
other? I’m not a fan of the cover up. Call it how it is.
The opener is weak & comes off as bulk email. What
exactly made you reach out?
This is a very sensitive issue & pretty presumptuous to
approach it in this way.
The subject line is lame, boring & overused. Saying
you did research is not the same as demonstrating it.
Asking if he’s the right person is your responsibility. Do a
quick search on LinkedIn.

12. Crappy Email #3
No one says ”dear” anymore – this isn’t a letter to
your grandma.
It looks like a bad info product ad from the 90s. It feels
sketchy & hard to read.
This is a very sensitive issue & pretty presumptuous to
approach it in this way.
I’d never read it because it’s too long. The bold & all
caps scream spam to me.
They show immediately they don’t understand me. Wait
for reps to sell the solution to drive interest.

13. Crappy Email #4
CEO to CEO email should be strong & confident.
Always have a proofreader.
This shows lack of email in grammar. There is zero
personalization beyond title & company.
Appreciate the attempt to build rapport, but it’s in the
wrong place.
They show immediately they don’t understand me. Wait
for reps to sell the solution to drive interest.
One paragraph doesn’t flow to the next – each has a
completely separate tone/feel. And that’s a terrible CTA.

14. Crappy Email #5
Tell me exactly how you helped someone like me.
Bonus points if it was someone in my network.
Why is the pitch last? I probably didn’t make it that far
because I wouldn’t just accept this offer to chat.
It was short & to the point, but if Charlie was the right
guy, it’d be good. Also, maybe use a Calendly link.
Way too long of a PS. It’s longer than the body of the
email!
“Given your role” isn’t personalization. It’s a cop out.
Why should I spend 15 minutes with you?

15. Crappy Email #6
It seems like an email with a CTA to send more info.
Have more of an ask than that.
The signature block is gargantuan & a turn off, especially
for someone who specializes in email marketing.
Love the stats. Unfortunately, with no personalization
as to why Engagio, it comes off spamy.
There’s nothing wrong with the 2nd paragraph, but it
adds no value here. Use it in the follow up instead.
I may be interested in the report, but not discussing it
yet. Also, do some more research.

16. Crappy Email #7
Avoid vague statements. If I have to think too hard
how to respond, I don’t respond.
Punctuation, grammar & fluidity are lacking here. Also,
it doesn’t say how they can help me.
Why would anyone want a demo from this person?
And a demo of what?
Why would Jon stop what he’s doing to explain how his
team approaches outbound?
1st sentence is bad. If I satisfied everyone curiosity
who sends me a cold email…

17. Crappy Email #8
Maybe highlight some quotes from the video that
would be compelling to the specific buyer.
This email is too pushy and feels desperate. There’s not
enough context to make the stat seem credible.
This specific use of links would make it go to spam.
Perhaps follow up with links if the person replies.
You lost me at the subject line. And if I’m too busy, why
would I watch a video? Take the time to personalize.
Nothing on the face of the planet increases win rates
by 83%, so someone is smoking something.

18. Crappy Email #9
It starts off strong but fails to tell me what they do. Real
time insights are great, but what exactly is that?
He didn’t respond because it was irrelevant. Try
different messaging or another value prop.
Did he get the email… of course he did! There are too
many reasons to name why he didn’t respond.
Raising funding is old. If You’re reaching out because we
raised money makes me think you don’t care about me.
It wastes valuable space with a throw away line. The
companies mentioned have nothing to do with Engagio.

20. Crappy Follow Up #1
No one says ”dear” anymore – this isn’t a letter to
your grandma.
Another vague, worthless email. No value. How
quickly will this get marked as spam?
Weird fonts & cold school ads are suspect. It doesn’t take
much effort to get your email up to 2016 standards.
Follow ups need more context. Remind them briefly
why they should connect.
Pretty much an empty email, but at least Nick got to tick
an activity as completed in his CRM!

21. Crappy Follow Up #2
The subject line is too vague. Remember, the subject &
the 1st 10 words is what you see on on preview.
Do everything you can to find out what’s important to
your prospect. Seek to understand them & their situation.
I haven’t responded to you once, I’m not going to send
you to someone else. Also, you can’t have 2 CTAs.
The entire email is very vague. There’s nothing
compelling about it at all.
No effort on the subject line. Nothing like the guilt “I
didn’t heard back from you.” Poor you.

22. The 1st sentence is too aggressive. I wouldn’t even be
interested in reading the rest of the email.
Tone is underrated in email – mind the tone. Avoid
making assumptions.
“Contact me to learn more…” Really? Don’t make your
recipient work. Also, provide specific benefits.
You’re emailing me, so you’re not holding off. It’s passive
aggressive. You haven’t earned the right to use that tone.
Crappy Follow Up #3

23. The lack of research is painful, as Jon founded Marketo.
“Faux” research comes across as disingenuous.
It’s a bad idea to knock competitors. Poorly creating
fear, uncertainty & doubt lands you in the junk folder.
It’s generic & doesn’t focus on a big enough benefit or
pain. It’s confusing what the company wants.
Be relevant by focusing on the pain you solve. Leverage
use cases & case studies.
Don’t be so formal. Write like you talk. I love using
contractions like “I’m” & ”we’ve.”
Crappy Follow Up #4

25. Top 10 Tips for Good Cold Emails
Write like you talk. Keep it conversational and sound like a person!
Always have one definitive CTA.
Don’t bash competitors. It’s extremely off-putting.
Emails should be in black text and a sans serif font. Anything else is
distracting and potentially unprofessional.
Never include large graphics, attachments, or signature blocks, as
they could be picked up in spam filters.
1.
2.
3.
4.
5.

26. Top 10 Tips for Good Cold Emails
Whenever you have a URL, shorten it usingTINYurl or Bit.ly.
Always proofread your emails.
Keep it simple. Don’t use buzzwords or industry jargon.
Write as if it’s being read on mobile. Use white space & more
paragraphs to increase readability.
Spend time on getting the subject line right. They are your 1st
impression & teaser for your email.
6.
8.
8.
9.
10.

27. How to Not Send
Really Crappy Cold Emails
Engagio.com/crappy-email-ebook
Get the full, unabridged version
with full critiques now.

28. Orchestrate human connection at scale.
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