Okay…we’re back. Our last episode covered why prospecting can feel rough. Why it’s not given enough attention and resources. The characteristics of inbound and outbound. And a rule of thumb for when to consider automation in your outbound motion. But we never really got to contrast more manual outbound approaches with industrialized ones. So let’s get to it.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your second installment.

Your two options in outbound are automation and account based marketing – also known as ABM. Account Based Marketing is a fancy-way of saying personalized outbound. You hand-select accounts you’ll be reaching out to, and find personalized ways to break into them. And initiate sales conversations with key stakeholders within those organizations. Some folks talk about their Dream 100 list. This refers to the top 100 accounts you’d like to start selling to. The customer logos that have you salivating for your startup. Building such a list is a great way for any startup operator to start their outbound motion. It dials in your focus and – when successful – allows you to build sturdy social proof. Envision being able to say, “Our product launched just 3 months ago, but Uber and Google are already customers of ours.” Stronger case for folks to pay attention to you, wouldn’t you say?

But back to personalization. Put simply: it increases your response rates. “Why?”, you ask. Well, because you’re gifting your prospect the feeling of being seen. Understood. Every human being has the innate desire to feel like they’re seen and accepted in their own uniqueness. As a salesperson, you’re tapping into that need when reaching out in a personalized way.

When you take the time to notice that your prospect has been to your favorite omakase sushi spot in San Francisco, you not only establish a kinship around your mutual love of delicious raw fish, but you also make them feel known. And you, in turn, get rewarded with a higher reply rate. Personalization also has the advantage of making each outbound message very different from the previous one. Which can play a huge role in keeping you out of spam. Remember: spam algorithms from companies like Microsoft and Google look for carbon copies of messages being sent out by the same inbox. And then penalize those senders for their carpet bombing. Personalization is the opposite of that. Each personalized message feels unique, and thus is very spam-friendly.

Account-Based Marketing also has a shorter time-to-value – namely obtaining interested replies – than automation. The explanation for that? As we just mentioned, when you send personalized messages to prospects, your response rates are typically higher. And those response rates will also often pull up interested reply rates. Think of it this way. Anytime you’re personalizing, you’re giving yourself a chance at a longer conversation. You’re driving up engagement. Your prospect is more likely to linger on your message and give the sales copy portion of your message a greater chance to land with them. So when done correctly, you’re getting your first few interested replies faster with ABM than with automation.

Here’s an email you could send me that would almost guarantee yourself a response, provided I saw it:

Subject Line: hot yoga in India, Paul…?

Hey Paul,

Couldn’t help but notice that you were a fervent yogi…have you considered doing a retreat in India?

[Sales Copy]

BTW: do you think Djokovic has a shot at breaking through for more Slams with Sinner and Alcaraz dominating the Men’s game right now?

So you seeing me as a yogi – and thinking that perhaps I’d be interested in doing a retreat at the practice’s birthplace is sure to elicit some emotion from me.

Now to the closing piece of personalization bookending the email. I grew up playing competitive tennis. I don’t play much anymore, but I follow the men’s professional game very closely. You calling out a major dynamic happening at the top of the men’s game – the elder statesman Djokovic staving off Father Time as he tries to break through Sinner and Alcaraz’s dominance – and asking my opinion about it is a sure fire way to get me leaning in.

Having read the message, regardless of what is being pitched, I’m going to think, ‘Man, this person gets me. They’ve taken the time to truly understand what’s important to me, what I care about. I owe them a response at the very least. Whether or not their product is relevant to me.’ And that’s exactly the kinds of thoughts you want your prospects to have when they receive a personalized outbound message from you.

By the way, this is how we teach personalization to many of our clients. A personalization layer at the top of the email to break the ice. And then one, as you bid them farewell, post call-to-action/offer. We’ve noticed that getting a least two in per email greatly enhances your chances at a response from folks.

Before leaving you this week, I’d like to illustrate how you should start thinking about automation or manual approaches with two extreme examples.

First, let’s imagine for a second that you were selling a product with an average ACV (average contract value) of $2M that was a fit only for Fortune 100 companies. And because of the nature of your offering, the only two job titles you’d want to target are the CEO and the CFO. That’s a total of 200 – 100 total companies times 2 job titles – possible contacts to go after. Due to the large average contract size and low number of potential targets, you could spend a huge amount of time and resources personalizing your outbound communications to each individual lead. ABM is perfect for that. I’d applaud a founder that would want to spend 2 hours crafting a handwritten message on parchemin paper that was to be delivered by private carrier. Or a startup operator that was to send one Air Jordan to a prospect with a penchant for sneakers with an accompanying note saying, “This is my way to get my foot in the door. The other shoe will drop when we meet in person 😉.” The key is: each introductory meeting booked is worth a lot to the startup selling here. Definitely worth wringing the towel dry to initiate the sales conversation.

By contrast, let’s now picture you’re targeting finance leaders at startups to sell them a product with an AVC of $12K. Doing a quick search in Amplemarket – our favorite marketing automation tool – for such leads shows us a total of 432,456 target contacts. For that vertical, automation fits like a glove. You’ve got a veritable ocean of prospects to go after. Because of the abundance of leads and low ACV, you can take full advantage of what automation has to offer. Namely, the fact that it’s a lot less resource-intensive. You could write up an automated email campaign, fill it up with leads, and send it off within 30 minutes.

For account-based marketing, our clients will generally spend 15 minutes sourcing a lead, researching it, and writing a personalized message before pressing “Send”. Automation is also far more scalable. In a matter of five minutes, you can clone a successful campaign and double down on it with twice the leads you had used in the initial sequence. And lastly, because of its scale, you’re able to get to statistical significance faster. Within 2-weeks, you can have a 4-step 100-lead campaign fully deployed and come to some conclusion on the messaging it contains and the persona you’re targeting. Account-based marketing doesn’t afford you that kind of statistical significance until you’ve put in a lot of work. Usually in the hundreds of messages sent out. At fifteen minutes per message crafted and sent out, that’s a bunch of time spent before being able to deduce much of anything from your laborious outbound efforts. I’ll let you run the math.

Now that we’ve covered our large scale options to put forth good outbound, how does one think about crafting a message to garner interest from a target prospect?

Well, the first thing to consider are the ingredients for this messaging. Just like it’s virtually impossible to make a great meal without good ingredients, it’s out of the question to compose a great message without good outbound copy building blocks. They fall in five different categories. And you’re going to want to have one from each category included in an outbound message designed to be a full pitch.

That’s where we’ll pick up our discussion next week. Join me as we review the five ingredients that enable you to make a delectable outbound message. You’ll leave prepped to start copywriting.