Email is an ad unit (and other advanced tips for outbound)

Several months back, I wrote about learnings I had garnered while building out outbound for Whitetruffle a few years ago, and with several of my consulting clients more recently. That first installment was meant for you to go beyond outbound best practices you probably read about online. The following is meant as a second chapter, weaving in even more advanced insights that weren’t included in the original.

Email is an ad unit.

Email is an ad unit, but it can take a moment to see why. Email feels invasive and superfluous. It infiltrates your inbox in overwhelming volumes. Some office workers view it as a to-do list that’s been forced upon them; touting their all-too-few “inbox zero” moments, which have become synonymous with peace of mind.

But thinking about it in such a way misses an opportunity to see email as a significant channel in your go-to-market arsenal.

How is email an ad unit, and a sophisticated one at that?

Email is a direct channel to a prospect transmitting a message that — if well-crafted — compels them to act. In most cases, this action is to (we’ll look at in the B2B sales realm, here) respond to the email and agree to an introductory call. When seen that way, email is a type of ad, that inspires its audience — the individual prospect — to act.

“What makes it a sophisticated ad unit?”, you might ask.

Well, email is incredibly personal. It is one-on-one communication that lands in an inbox that belongs to you and you alone. You get the sense that the author is writing to you solely, and to no one else. This creates a sense of intimacy that a billboard in Times Square, or a radio spot on national airwaves will never possess. Even when you’re broadcasting email to your targets in massive email campaigns — if done right — it feels like narrowcasting to each individual prospect. Or at least, it’s supposed to feel that way. More on that later.

Second, email is targeted to the utmost. You chose your targets in your lead generation process. You defined your Ideal Customer Profile based on who you believe is your ideal buyer, before even sourcing your leads. You know exactly who will see your messaging down to the company, job title, first, and last name. With other forms of advertising, you’re not quite sure who gets to see your ad. If you’ve bought space on a billboard along the 405 in Los Angeles, you can only hope your message hits folks that are likely to buy. But, you have no assurances. Same goes with radio advertising. Or TV ads. This leads marketers to utter John Wanamaker’s old truism, “Half the money I spend on advertising is wasted; the trouble is I don’t know which half.” Email is just the opposite. You know exactly who the recipients will be, and provided your customer profile is dialed in, there’s little wasted money or impressions.

Third, you have the benefit of knowing you can have several, more in-depth interactions with your prospect with email. With a good chunk ad units, you’re lucky to get one interaction: an impression, and if you’re lucky perhaps a click. Even when retargeting digital ads, you might get a few more clicks on the ad over the lifespan of the cookied user. But you won’t get the breadth and detail of feedback you might get through email. For broadcast media, like radio ads, it’s very hard to even track the effectiveness of your ad units. You buy ad units on a broadcast outlet, your ad is read on the air, but you rarely get feedback on your messaging from the prospect. More often than not, it’s very difficult to even track the impact of those types of ads. With emails, not only can you track the effectiveness of your messaging, but you can have several exchanges with the prospect. You are getting more feedback on your messaging per impression, than virtually any ad unit. Did you happen to leave your prospect confused with the value propositions you put forth? Were you able to clearly and concisely express how your service differentiated itself from competitors in the market? Were the value propositions you led with in your messaging the same ones that led your prospects to buy? What short message will likely grab the prospect’s attention? Responses from prospects to your emails act as direct feedback to your messaging. They let you know if they are confused at how you describe the main value proposition, or how you differentiate from the competition. You’ll be able to take those responses and iterate on your messaging. When your email messaging becomes crisp, you will know it. And you’ll be able to use the messaging company-wide. It’s wording you’ll work into ads, marketing communications, press releases, investor pitches, etc.

Fourth, email has several different components you can optimize for best results.

The first component is the subject line. That’s your business opener. Your pickup line. If you’re unable to get people to open your email, it doesn’t matter what you have in the email body. The email could very well be blank, if no one opens it. When I run campaigns, I try to hit an open rate of at least 40% (for the entire campaign) before focusing on the email body. You have very few characters to work with, so it’s important to be compel your prospect to click on the email. I’d encourage anyone to play with many different variations early on in your outbound buildout. When the data comes back, pick out the best performing subject lines and build around those.

Once we’ve hit that 40% open rate marker, we can focus on the second component of our ad unit: the email body. The copy contained within the body of the email is supposed to pique the prospect’s interest and get them to book an introductory call with the sales rep. You can be lengthy here, but it’s actually recommended to keep things short, sweet, and — believe it or not — informal. Getting a call scheduled for a rep or a founder contains two main conversion points. One is an actual response — an event we try to get at least 6% of the time, for the entire campaign. The other conversion point is an interested response — one that is captured by the Interested Rate. We try to hit an Interested Rate of 2-3% overall. The Interested Rate the most single important metric in outbound, as it represents the number of interested responses you’re getting back from prospects. Although we aim for a 2-3% conversion rate for interested replies, anything over 1% is considered a successful campaign.

The complexity of email is the reason why I never start out sending out large campaigns when I do an outbound buildout. Cranking things up prematurely will only cause you to burn through a large amount of leads prematurely. Early campaigns should range from 50 to 150 emails. Never more. Once we reach 1% interested rates, then we’re ready to scale things up. Before then, it’s premature. Unless the company has short term revenue targets to hit. That’s the only exception we’ll make. We’ll sacrifice leads in order to hit those targets, if need be.

If you allow yourself to look at email as an ad unit, it will brighten your outlook on it and make you a better email marketer. Email has been under fire in recent years. Folks in Tech have been clamoring for a better alternative. Meanwhile, email seems to be doing perfectly fine, as a mode of communication. Viewing it as an ad unit will allow you to become sophisticated about its various components, and allow you to craft more personal, punchy messaging that will generate more interested responses, and consequently, more intro calls.

Now that we’ve got you engaged about the medium, let’s get into some practical tips about how to make your outbound more effective.




Leverage founder-to-founder (or CEO-to-CEO) empathy

A few months back, I was working with a client on their outbound buildout. We had been slaving away at it for a couple of months. But, we weren’t hitting our conversion metrics. More specifically, we were having a hard time getting prospects to respond favorably to our content. Our Interested rates and Response rates were far too low.

In an attempt to change our fortunes, we decided to think about the problem differently. Instead of targeting Product Managers with a sales rep, as we had up to this point, we thought to ourselves, “Why not try leveraging the inherent kinship that exists between fellow founders of startups?” My client — a start-up — had a founding CEO with a good reputation and friendly demeanor. When I first brought up the idea of using him as our outbound point of contact, he was not convinced. I had to cajole him a bit, into trying this new idea. I pushed forward, “Listen, why don’t you let me run this campaign? We’ll create a new email address for you, and I’ll manage your inbox. I just want to be able to use your persona and establish some kind of connection with these folks. It will be a welcome departure from what we’ve been doing. We all know PMs don’t want to talk to a rep.”

He finally relented. And our new campaign was off and running. Within a couple of weeks, we knew we were onto something. We were finally getting responses back. Folks were actually interested in booking introductory calls with us. We had gotten our foot in the door. A large victory, for this client.

Now, why did this work? Why would a founder respond favorably to another founder?

There’s an inherent closeness between founders, that’s been forged by common intense experience. Despite working for different companies, you’re in the same foxhole together fighting the good fight. It’s you versus the world. You’re the anti-establishment new kids trying to bring down the industry incumbents with your radical approach. Very few people can relate to the pressures you face on a daily basis. You have to answer to your customers, investors, and employees. You have managed to build a business out of thin air. This extreme life you’ve chosen it not one many can stomach. Those that do take the leap automatically recognize one another. The bond is unspoken and already exists. All you need to do is remind your fellow founder that you’re here, and in it with them.

This approach works with CEOs as well, by the way. There, the kinship has a similar flavor. Even if the CEO hasn’t founded the company, it’s a lonely role at the top of a company. CEOs tend to understand one another, and bond at a very basic level.

Here’s an example of founder-to-founder copy that has worked in the past for me:

Hi {{first_name}} – I’m reaching out as a fellow SaaS founder to chat about ways to make [short phrase about high level value props]. I’ve been aware of what you’re up to and I’m interested in helping.

I’ve founded two companies ([Company1}.com and recently [Company2].com) and bootstrapped them to scale (X+ employees currently) by helping out other SaaS companies [do what your company does].

If we’ve piqued your interest, our team would be happy to chat sometime and offer some informal feedback.

What do you think?

Ask for feedback as a call to action in your email.

As you may have noticed in the copy example above, I am not selling hard. It feels a lot more informal. More, “let’s have a cup of coffee” and less “let me give you a presentation on the stellar benefits of our solution”.

One of the ways you get into the good graces of people is by asking for feedback rather than offering it. It’s a great conversation starter. People love giving it out. You’re propping up your prospect as an expert in her field. And you’re putting yourself in a humble and vulnerable position.

Anyone with a good conscience will most likely be swayed into being a good samaritan and help you out. And with that; you’ve got a conversation with them. Because you’ve made the prospect comfortable and valued, there’s a great likelihood they’ll start opening up about their issues. And all of a sudden, you can start soft selling based on what the prospect is confiding in you. You’ve built a trusted relationship with someone that was initially a cold prospect. If you’re subtle about it, the actually selling become the easy part. It’s all downhill from here.

Here’s an example of email copy I have used to ask the prospect for feedback:

Hi {{first_name}} – I’m a fellow founder looking for a bit of feedback on my new product: a way to [Short pitch about what the company does]. It’s like [Example company everyone knows], but [A different market].

Do you have one ‘wish list’ of features you’d like to see for what we’re building?

For background, we’ve helped companies like [Example Customer A] and [Example Customer B] add more [High level value prop] in a few weeks.

I’m trying to build a list of the most requested ones – so any feedback would really help 🙂



So next time you’re having a hard time booking calls with your current email copy, throw in a feedback request, and see how that works for you. In the startup world — where folks are always curious about new products and new trends — there’s an even greater chance you’ll get a favorable response from a fellow alpha user. And starting from a place of feedback will allow you to sell more effectively. Next thing you know, they’ll not only open up about feedback on your product, but also on the needs they have as a company.



Do not try to sell your product or service in one email.

In sports, there is such a thing as “trying to do too much”. At times, in baseball, the correct percentage play is to bunt the runner over; not swing for the fences. At certain situations, in football, all you’re looking to do is to get that first down, move the chains and buy yourself a new set of downs. You’re not looking to score in one play when you’re backed up at your own 10-yard line.

In the very same way, in outbound email campaigns: don’t try to get the transaction with one cold email. That’s simply unrealistic. Even asking the prospect to sign up to a free trial is asking too much, in many cases. Your goal should be to generate an introductory call.

That’s it.

If you start thinking about selling your product outright, your copy will be too long. Your message will be diffuse. You’ll run the risk of losing your reader in long feature lists and other benefits. Your message will most likely come off as a hard sale. Instead of bunting the runner over, you’ll end up striking out because you wanted to hit the ball out of the yard when all you need to do is get a runner on base.

Here’s an example of email copy that tries to do too much right off the bat:


I am reaching out because we’ve developed innovative software that will alleviate your headaches as a CFO.

Our software enables large companies to reduce their accounting costs by 68% on average, by reducing the amount of manpower needed and by increasing efficiencies.

Companies like Apple, Google and Facebook all use us, and have all expanded their relationship with us over time.

We’d like to include you to our client list. Feel free to get started with a free trial here.

Let us know if you have any questions.



If I were to be approached by this type of email, I would be very much turned off by it. The sales rep has no intention of getting me on the phone, nor the willingness to answer any of my questions. Nevermind do a demo of the software. The email does a good job of establishing credibility and social proof, but it falls short in that it tries to convert me right away without offering to handhold me through the process. This is an example of an email that tries to get to the free trial too quickly. Even folks that don’t like to chat with sales reps will feel a little awkward by the above approach. You might get a few folks to convert to a free trial, but the vast majority of folks will not react well. They more than likely won’t click on the link, nor will they respond to your email.

With a few small changes, the email copy becomes more palatable to your prospect, and increases your chances of eventually closing them:


I am reaching out because we’ve developed innovative software that will alleviate your headaches as a CFO. And we thought this might be relevant for you at [Company].

Our software enables large companies to reduce their accounting costs by 68% on average, by reducing the amount of manpower needed and by increasing efficiencies.

Companies like Apple, Google and Facebook all use us, and have all expanded their relationship with us over time.

What’s a good time for a quick introductory call next week?

I’d love to learn more about your business and see if we might be able to help.




If you start thinking that way — getting that critical first down instead of throwing up the Hail Mary — your copy will reflect that. It will be short, crisp and to the point. And your prospect won’t feel like you’re moving too fast with them. The email’s sole purpose will be to pique your prospect’s interest enough to have them agree to a quick call.

Commodity products or services will (most likely) not get high response rates.

One of the keys to outbound emailing is that you grab your prospect’s attention. First, with your subject line — to generate an “Open” — and then with your email body — to generate an interested response.

Imagine trying to grab your prospect’s attention if you can’t differentiate. Without being able to stick your neck out and say, “this is why we’re different and better than the competition.” Without telling them first why you are worth paying attention to, and then why you are above the competition. Products or services that are commodities — undifferentiated, for the most part — are invariably going to struggle with outbound email.

As an example, if you’re a development shop, and you’re mulling over whether or not to do outbound, think again. Even if you’re faster at deploying features, or more rigorous about doing QA, there’s a good chance that’s not a strong enough differentiator to tout over email and generate interested responses. You might be much better off relationship selling with a charming salesperson that will make friends with your prospect and inspire them to sign by their very likability. The differentiator — in this case — will not reside in the service, but in the salesperson.

Do not use calendaring software to schedule the initial call.

It’s one thing to use a calendaring tool like Calendly with an inbound lead. You have strong intent from the lead. They are very interested in having a conversation with you, as they have taken the time to fill out a detailed online form. Although I don’t always recommend it even in this scenario, you might well get away with it for that reason.

When it pertains to outbound, sending someone a calendaring link asking them to do the scheduling with you themselves is never a good idea. And yet, people do it, these days. Let me remind you: as the sales rep, it is your job to chase after the prospect and earn their business. Sending a calendaring link puts the onus of scheduling your first real interaction on a prospect that has just been cold emailed. It’s just not a good look to ask them to do that. Bad form very early on. As they are mulling over whether or not to answer your cold email with some interest, you are then asking them to take on the extra work of looking through your calendar and booking a time.

Always do the work of scheduling the introductory call with the prospect. You’ll start the conversation on the right foot.

Make sure your first line or two of email body copy are attention-grabbing.

You might say, “Well, that’s not really insightful. Everyone knows you want to hook people early on in your copy.”

And you’d be right.

The insight comes here, however.

Imagine yourself in the following situation. You’re having a very busy Monday. Your boss is on you about a report you’re behind on. Around 12:30pm, in a small gap between calls, you decide to pop out of the office to pick up some takeout from the nearest food truck, a few blocks away. As you arrive, you wince at the line that has already gathered. You bite the bullet and opt to wait the 10 or so minutes it will take to finally order your food. In need of distraction, you naturally look down at your phone and check your email…

This is the typical scenario you need to think about when generating email copy. The subject line and email body copy must be so good that it would grab the caffeinated, overworked version of yourself during a quick lunch break and prompt you to respond with a time for an introductory call.

Layer on the fact that you’re working with limited real estate on mobile devices, and you’ve got to make sure your copy is attention-grabbing right out of the gate. Not in your fourth or fifth sentence. But more like in the first.

The message needs to be punchy early. And it needs to compel your prospect to keep reading and then respond in a favorable manner.

Here’s how this translates to your email copy writing. Reduce your pleasantries up top. Nobody feels like you truly care when “you’re hoping they are doing well”. Get to the point. And lead with your best value right away. Do away with product features or functionality. Folks don’t buy products because they have features. Lean towards being very direct, even if it initially feels uncomfortable at first. You want folks to be able to read your first couple of lines on their cell phones in-line at the grocery story and respond with times to connect by phone before they get to the cashier.

An example is useful here:


Is [Company] spending an inordinate amount of time identifying clusters within customer behavior?

Acme’s interest-driven analytics engine will take care of that for you.

For example, our customer [Example Customer A] found new user clusters in 10% of the time it would have previously. WIthout doing any of the manual work.

Could this tool be useful for [Company]?


When you next find yourself working on email copy, visualize yourself as that stressed office worker taking a fifteen-minute break to pick up lunch. Can your copy be good enough to capture that person’s interest as they wait in line, and have them respond with times for that first call?

Outbound is one of the most rewarding things you can do in sales and marketing. You go from having no conversation going on to knocking down a door, and getting yourself in front of the prospect. Before building out outbound, you had no way to pitch your product or service. With effective outbound, you get yourself a ton of at bats and a chance to materially affect revenue. With that in mind, make use of the above tactics and the ones you might come up with. Let us know how they work out for you.