Cold Emailing

It was his seventh unanswered touchpoint to the president of a massive food distribution company. “It was my first cold email to him,” he recalls. “We never connected on the phone. There hadn’t been any communication.”

Then, the breakthrough:

And with that, Mr. President CC’d a relevant decision maker.

The rest of what went into closing that gargantuan $30 million deal is history. But that one cold email, and his persistence to power through the radio silence, catapulted James into the hallmark deal of his career.

“Every and any cold email you send is a lottery ticket,” says James.

Email offers unlimited potential; it’s the number one channel for engaging your prospects and it’s why 96% of sales teams use it across their outbound outreach.

But most of these teams misunderstand the fundamental goal of an email.

The primary goal of a cold email isn’t to:

• Establish your value ❌

• Book a meeting ❌

• Or close a sale ❌

The primary goal of a cold email is to get a response — to jumpstart a relevant buying conversation, and to ultimately enter into a mutually beneficial relationship. Very few people are open to sacrificing 30 minutes to meet with a complete stranger; many more are willing to spare the ten seconds it takes to reply to a well-written, pertinent question.

Aiming for the response affects everything, from your email’s verbiage and tone to its calls-to-action and all the interactions following.

In this section, we’ll show you how to apply the philosophy of Full-Cycle Selling to your cold email outreach by teaching you:

1. How to personalize your outreach

2. The anatomy of a successful email

3. The three-email structure that gets phenomenal reply rates

Leandra Fishman, CRO at Apollo and former SVP of Sales at Twilio (NYSE: TWLO) and CRO at Intercom, gets hundreds of emails a day. The ones she chooses to open, read, and respond to are few, and they have two key qualities:

1. They have some level of personal connection to her (personalization)
2. They uncover a timely problem for her and present a solution (relevance)

“Nailing the cold email requires both personalization and relevance,” she says. “If emails are written in an obviously generic way, I am not replying. If they reference something too obscure or generic, then I’m also not replying.”

Email personalization and relevance is non-negotiable for every prospect. But the level to which you personalize, and the amount of research and preparation that goes into every email, will depend on the value of each lead.

So pull out that lead prioritization framework. We’re going to go into detail on how to personalize emails across each tier of lead.

For your Tier 1 prospects like Leandra (your highest-level decision makers, your champions, your best-fit leads, and biggest opportunities), you’ll want to dedicate the bulk of your time to manually writing your most personalized, thoroughly-researched emails.

Contrary to popular belief, C-suiters are nearly just as likely to open and read your emails as less senior personas. Across 976 million Apollo emails sent to founders over a six-month period, VIPS, and C-Suite executives, open rates were 21% — only 2% less than lower-seniority personas.

You have their eyes. Don’t waste the opportunity by dumping them in generic, auto-email campaigns.

Samantha McKenna, one of the best cold emailers in the world and former Director of Enterprise Sales at LinkedIn, built and scaled a 7-figure business by handwriting emails to VIP prospects using a strategy she calls “Show Me You Know Me®”.

“‘Show Me You Know Me®’ is the art of knowing your buyers as humans...and it trickles down to every single touchpoint you have with your buyer,” says Sam.

Emails worthy of your Tier 1 prospects start and end with research — really, really good research that spans across a few key channels and uncovers information you can directly reference in your emails to — well — show them you know them.

Sam says there are three layers to researching and understanding your top prospects before you reach out (see figure 3.1).

1. Research the human

“First, what do we know about this person as a human being? What common ground can you find to authentically connect?” says Sam.

To get a better idea of who the heck this person is that you’re emailing, start with a simple search in Apollo. From their contact page, you can find work history, technology used, intent signals, previous engagement with your brand, or any existing notes or activities.

Then, go a little deeper. Uncover more about their personal life on LinkedIn. What do they post about? Who do they follow? What are their skills, hobbies, and interests? If they aren’t active on LinkedIn, a five-minute Google search could unearth some of this, too.

2. Understand the company

Next, uncover more about their company with a thorough review of their website. What exactly does their product do? What are their values? Who do they help?

Sometimes, you’ll even find that executives are participating in upcoming podcasts or events that are advertised on their site. Take note of this and use it to add more fuel to the fire.

3. Learn the space

In her early days as a rep, Sam’s company had three of the largest law firms in the country as customers. There was a huge opportunity to target more, but in order to sell to a room of legal minds, she needed specific knowledge of the vertical. She set up interviews with their current customers to understand why they used her product, why her company was important to them, and the vernacular of the industry (lawyers use the term “clients” instead of “leads,” for example).

Hands-on research gave her the industry expertise to go outbound and, over the course of less than two years, she expanded the company's vertical by 1,333%, adding 40 new law clients.

It’s hard work, but a commitment to researching before engaging, before you ever send that first email, is what it takes to sell like the best.

Bringing all of your research together into a perfect “Show Me You Know Me®” email looks something like figure 3.2

It’s a little long, but in Sam’s experience, a long email with the right personalization can earn a lot of replies — especially with your highest-value leads.

On top of being the most personalized email the prospect has likely ever received, it’s hyper-relevant. It weaves together all of the research you’ve done to highlight their problem, how you can fix it, and shows them you’ve done your homework.

Voila! Relationship begun.

In an ideal world, you could write a Show Me You Know Me® email for every prospect, but depending on the size of your audience and the information available, you may not have the time to spend 20+ minutes per email. For your Tier 2/3 leads (you have up-to-date contact information for them and they align with at least one or two relevant signal filters), the key is finding ways to be relevant and to personalize at scale.

This is when automated email templates come into play.

By sub-segmenting your lead list based on signal filters (i.e., recent acquisition, job changes, funding, industry, etc.), you can use customizable email templates to speak to something that’s relevant to the whole segment.

The trick to fantastic email writing for your Tier 2/3 prospects is to get straight to the point and pack as much value as you can into a few short, clear sentences.

Let’s say you just started your work day, you’re making your way through your email inbox, and open one that looks like figure 3.4.

Would you read it?

…We wouldn’t either.

This email is long — way too long. In an analysis of the highest-performing cold emails, Apollo’s advisory board found that the best email bodies rarely contain more than 100 words (with the exception of those hyper-personalized Tier 1 emails).

The person who wrote this email asked me for advice on how to fix it. Here’s what I told her.

“People don’t want to read an email of this length. But, let’s say someone does read it. The other issue is that it’s all about you, the sender.”

Your potential buyers don’t care about you. Harsh? Maybe, but that’s the reality of sales.

Your email recipients are focused on themselves, their goals, and the problems they are facing right now — as they should. If your message is all about what you do, what you want, and what you think they should do, you’re already misaligned with your buyer before you ever talk to them.

Be relevant, be brief, and be about the recipient.

If you’ve experimented with ChatGPT at least once or twice, you know it can’t spit out full emails without sounding like AI, let alone uniquely personalize them.

“AI-generated copy is so hot: everyone wants to use it to create messaging. But nobody wants to consume AI content,” says Florin Tatulea, Head of Sales Development at Common Room.

AI-generated copy just doesn’t have that human touch, and your prospects can tell. In a recent Apollo survey, 70% of respondents said they can easily recognize when something was written by AI. It can’t completely take email writing off of your plate, but it also doesn’t mean it’s useless.

We ran an GPT 4, AI email writing experiment to pit the hottest AI tools against each other: ChatGPT, GPT 4, Copy.ai, Lavender.ai, and Apollo AI. We started by feeding each one a detailed prompt using data we pulled from Apollo:

It’s not terrible. But is it the best email we’ve ever seen? Not quite. You would still need some tweaks to make it more buyer-focused. It also took about seven minutes to get to the final result. For an SDR working 200 to 300 leads, that’s anywhere from 1,400 to 2,100 minutes of time spent.

After generating nearly 100 emails across these five tools, we concluded that there are two key ways sellers can leverage AI:

1. Feed your email framework to the system with a prompt, along with examples of tone and voice (which is still hard to scale)

2. Use it as a starting point for your email copywriting

“AI is only as good as the data you have. Use AI as a starting point here and then take the time to actually adjust it yourself,” says Florin.

Still not sure where to start with your email copywriting? Don’t worry.

I’ve used a simple, three-step email structure to create relationships and grow outbound at numerous companies (see figure 3.6). With this series, I’ve seen reply rates as high as 34% over the course of a full month:

In this section, we’ll cover how to write three types of cold emails that, when combined, give you the best shot at getting replies and kicking off a new relationship:

1. The intro email. The highly-personalized first impression and where you’ll spend most of your time
2. The follow-up email. The short tidbit that resurfaces the first email
3. The breakup email. The last-ditch effort to solicit a reply

The first time you email a prospect, it needs to be personalized and relevant. It shows your prospects, including those busy C-level execs, that you’re out for a mutually beneficial relationship, not their pocketbooks.

You begin with the subject line.

Click-worthy email subject lines

Brilliant emails go unread without a good subject line.

Samantha McKenna has a few tips for replicating her unheard of 43% open rate — specifically for your most valuable, Tier 1 prospects.

• Your subject line should make sense only to the recipient

• Shorter is not always better

• Use “+” to break up the subject line

She gives an example of what would work on her: Switzerland + Le Dip Cheeseburger + {{your company name}}

What the heck does that mean?

Exactly.

This subject line is hyper-personalized to Sam. A few minutes of LinkedIn research would reveal that she’s Switzerland-born and a huge proponent of the cheeseburger at Le Diplomate in Washington, D.C. “Now, your company name won’t make sense to me. But the first two things do,” says Sam. “This will get me to at least open your email and see what you have to say.”

Harry Sims, former SDR Leader at Scratchpad, loves this strategy because it combats inbox autopilot. “Pattern interruption should be your first battle,” he says.

For prospects of lesser value, your Tier 2s and Tier 3s, your subject lines still need to be personalized, but you can afford to take some shortcuts. Many sales engagement platforms have personalization tools like dynamic variables. Plug in fields like {{first_name}}, {{company}}, or {{location_city}} to automatically pull unique data on each prospect into your subject line.

The Apollo marketing team has tried and tested the impact of using simple personalization variables in the subject line. We found that it yields a ~15% increase in open rates.

As you move into writing your body copy, the same principle applies…

The body copy: To hyper-personalize or not to hyper-personalize?

In the creation of this book, we surveyed hundreds of sales leaders, analyzed millions of data points, interviewed dozens of sales experts from VPs to ICs — and one theme turned up time and time again:

Personalization matters more than ever.

This isn’t anecdotal. McKinsey found that over 75% of buyers are more likely to purchase, repurchase, and recommend companies that deliver personalized messaging (see figure 3.7). Not to mention, the companies that excel at personalization see a 40% lift in revenue.

Personalized messaging quite literally earns you the attention of your buyers. But creating those experiences across hundreds, if not thousands, of leads can take a lot of time.

How do you create unique and relevant messages in every email send?

Prioritize the bulk of your manual effort for the leads that matter most, and use automation for the ones that matter less.

Consider this high-level personalization framework shown in figure 3.8 (if you need a refresh on tiering, revisit our section on lead prioritization):

Nadeem Elborno, who has an extensive tenure building sales orgs at Fortune 1000 companies, uses this framework to help his reps allot their time to the most profitable opportunities.

“A common mistake SDRs make is treating every lead the same, but 80% of your revenue comes from the top 20% of your customers,” says Nadeem. “You have to tier your accounts to figure out which ones are deserving of hyper-personalization.”

Chances are, you don’t get a response from the first message. Even the best initial cold emails can have a response rate as low as 1% — but that’s what a strategic, multitouch email campaign is for.

The goal of your second email send is to get a response by briefly resurfacing your first relevant message. That’s done in two ways:

1. Directly responding into the thread

2. Throwing out a quick, one-sentence question that can be answered with a “yes” or a “no” (see figure 3.9)

Skip the “hey, just following up” or “just checking in,” and simply restate the question you asked them in the first email.

If they reply with “no,” it’s not a bad thing. Of course you want a “yes” — that’s what fills your pipeline today — but pipelines are also built by prospects who say “no, not right now” or “check in with me in six months.”

No’s are victories, too.

Giving people an out to say “no” is one of my preferred methods to solicit more replies, which is good for your deliverability and sender reputation. With this structure, I often get more replies to the second email than to the first email. It shows the value of following up!

Sales executive Juan Ignacio Gallegos and the sales team at Requordit use this exact follow-up email strategy to secure a 48.5% open rate.

The follow-up email is also a perfect one to automate.

Karl Kwarnmark, Head of Sales at Talent Venture Group, saw a 17% reply rate on brief, personalized follow-ups — sprinkled with a dash of social proof — that automatically fire after three days of no reply.

“A light follow-up with a little social proof works great,” he says. “Something like ‘We’ve helped this company do X. Is this something you’d like to try out?’”

So, you send the second email and all you hear is *crickets*. What now?

The third email in this structure is a “breakup” email, your last ditch effort to solicit a response (although, by the third email you should have already called them and made a LinkedIn touch — more best practices on that soon).

The definition of insanity is doing the same thing over and over again — we know this. So for that final email, there needs to be a different approach, a pattern interruption, a dash of shock factor.

There’s no one right method, but we’ve found one that works wonders:

• Re-state the value from the first email
• Then give readers a laugh

Which might look something like this (see figure 3.10):

This email uses the same basic principles as the first email. It briefly states relevant value and ends with an open-ended question that prompts a response. But then! There's the hook, buried in the P.S. — a mysterious unrequited love set against the backdrop of an obscure tropical paradise.

What?????

You’ve just thrown something at them that they’re not expecting. In the same way a rowdy group is silenced by a sudden clap or your jaw drops in a movie’s big plot twist, you’ve used pattern interruption to claim back their attention.

In this case, you’re hoping for a laugh and often what happens is they respond to the joke itself.

Jon Selig, former stand-up comedian turned sales guy, says humor is one of the easiest ways to build rapport with prospects. “Using humor in a clever way, designed to elicit a smile, paints a memorable picture — and not necessarily because it’s always 'laugh-out-loud' funny — but because it’s unique from all other messaging your prospect receives,” says Jon.

Jason Westbecher, CRO at TrustArc, put this to the test and closed a $16k deal from email using Jon Selig’s strategy for pattern interruption.

Using humor might ruffle a few feathers, but there will always be people who don’t appreciate your messaging or style of outreach. The important thing is that you’re using strategies that are worth their weight in responses.

The three-step email series could work for you, too — the data certainly suggests it would. But don’t forget that your industry and target audience are unique. You may need to explore other strategies to find the approach that’s right for you.

“There’s no longer a set strategy,” says John Barrows, Founder and CEO of Sell Better by JB. “You have to be agile…Treat everything as an experiment.”

Use A/B tests to experiment. Try different subject lines, body copy, calls-to-action, and timing to learn what resonates with your audience. When you find something that works, repeat it.

Juan Ignacio Gallegos, Sales Executive at Requordit, goes as far as A, B, C, D, E and, you guessed it, F testing his email copy. It’s allowed him to learn from and iterate on his email outreach, eventually honing in on a variation that holds a 53% open rate.

Whether you’re emailing a Tier 1 prospect, a Tier 3 prospect, or your favorite celebrity hoping they finally read your fanfiction, these foundational email best practices will give you the best shot at a response.

1. Personalize manually where you can, and automate where you can’t

2. It’s OK to use AI, but don’t rely on it. If you’re facing writer’s block, try it for creating email variations and generating new ideas

3. A/B test to optimize over time

Perfecting the cold email is a one-way ticket to a bigger, stronger pipeline — but if you stop there, you’re leaving money on the table.

Take it from Nick Feeney, the VP of Revenue at Loom: