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.

How to take your outbound sales to the next level

You’ve just figured out an early path to revenue. A basic way to sell your product. It’s not a bulletproof process, but it has garnered you a few logos on your site, and a couple of testimonials from happy customers.

You’re thrilled that your new product is starting to get real traction. The gestation period — the twelve previous months of product iteration — are finally starting to pay off.

To get here, you’ve relied on introductions from friends, fellow founders, and your investors to get you in front of prospects. This is great; but you know it’s not scalable, and you’re getting the sense that your network will soon be tapped out.

How are you going to go from a handful of paying customers to your first 50 or 100?

I’ve found that an outbound strategy is one of the best ways to get you in the door with a large number of potential buyers.

I didn’t fully realize the power of massive outbound until I was at Whitetruffle and in charge of building out the top of our sales funnel. As Head of Sales, I had established a reliable sales process. We were closing business at a good clip, once we came into contact with prospects. What I was missing was a predictable way to get in front of a large number of potential customers. That’s when we started to take a serious look at outbound. 6 months later, our initiative hit its stride. Once it did, it was a veritable infantry. June 2015 saw us have our highest nominal growth month, and we crossed the $100K MRR plateau. 50% of our MRR growth in June was attributed to our outbound efforts.

At that point, I was sold.

And the beautiful thing about outbound is that when it’s humming, it’s entirely predictable, as Aaron Ross covers in his book. You know that adding X leads at the very top of the sales funnel will garner you Y in incremental MRR at the very bottom.

That kind of reliability is exactly what you want as a sales leader or CEO. Board meetings get a lot less painful when the forecast you’ve given your investors actually hits.

Having now built out outbound for Whitetruffle and for several consulting clients, I’ve gathered a few insights along the way. I’ve tried to stay away from the basic best practices covered in depth elsewhere, and focus on what I’ve been able to learn that wasn’t initially obvious. Here are some learnings to consider.

Be patient, but resilient. Outbound can take a long time to get right.

At Whitetruffle, it took us about 6 months for our massive outbound initiative to really starting firing on all cylinders. I usually tell folks I work with now to plan on at least 3 to 6 months before massive outbound clicks in.

There are plenty of variables to test in outbound:

  • Subject Line
  • Email Body Copy
  • Calls-to-action
  • Targeted Decision-makers
  • Email Campaign Length
  • Geographical Regions

Iterating on these can take quite some time. Particularly when you factor in that the first few weeks are usually dedicated to subject lines. And that most campaigns take a minimum of two weeks to finish.

Iterating on your targeting is key.

At Whitetruffle, it took us several months to really nail our outbound initiative. In June of 2015, after 6 months our outbound initiative finally ended up contributing to half of our new business and our highest MRR nominal growth month in the company’s history.

What happened for us to get there?

We had to iterate on market location and decision maker. We also had to find the right type of customer: folks that could buy and stay with us for a while. Factors like company size, churn, targeted decision maker are all things to think about and iterate on as you move forward with your outbound campaign.

If you’re selling a software solution to CIOs of tech companies, you probably will want to target tech hubs in the United States and across the globe. Think San Francisco, New York, Austin, London, Berlin. If you’re selling fishing equipment to fishermen, you probably want to stay away from the state of Iowa or Belgium (all land-locked regions).

When thinking about who to target within an organization, asking yourself this, “Is responding to email part of their job?”

The other day, I was talking email marketing strategy with my friend Conor Lee, CEO of HipLead. We were discussing how best to think about targeting decision makers within an organization. In our conversation, we were enumerating the pros and cons of reaching out to certain types of decision makers. In his inimitable way, he immediately distilled how one should go about thinking about targets: “If their job is to respond to email, you’re going to get higher response rate.”

Software engineers are known for not liking email, for example. They tend to be in a lean back posture and can take up for several days to respond, if they even do so. That’s because they rightfully make their living in their code, actually making product (plenty has been written about the Maker’s Schedule). That’s where their bread is buttered, every single day. Salespeople, on the other hand, earn their paychecks (and commissions) by being very responsive to incoming emails. Over the years, it has been drilled into them to respond as promptly as possible. Closing the next deal may well depend on it.

All things being equal, you’re going to want to go through a salesperson versus an engineer. The salesperson is much more likely to respond and get the conversation started. Even if they are not the person you’d like to interact with in the end, they’ll most likely get you where you need to go.

Here’s a different framework, that is useful, as well: “Is this person spending a considerable amount of time in front of their computers at work?” Folks that spend a lot of time at their desks are more likely to respond to your incoming emails. It’s one of the reasons you’ll undoubtedly have more luck in engaging with folks with office jobs versus local merchants, for example. Local business owners are more than likely going to be knee-deep in operations throughout the day, and away from their computers. The average office worker is going to have more screen time, and thus more opportunity to process and respond to email.

It was a lesson I learned the hard way, when selling a real-time mobile offers solution to local mom and pop shops in San Francisco back in 2011. I had co-founded BeThere and was eager to get our product in the hands of location merchants. It became quickly apparent to us that getting to them through email was going to be close to impossible. They weren’t responding to our emails. We started calling them and showing up at their businesses. It was a game changer. We were able finally engage them around our value propositions. And we quickly signed up 30 merchants across the city.

Make sure you are ready to scale things up.

This might feel a little bit obvious, but I have worked with companies that either hadn’t defined this Ideal Customer Profile, didn’t have enough sales interactions under their belts, or didn’t have the sales infrastructure (people and tools) to handle the increase in demand that an outbound initiative will provide you. Before you launch massive outbound efforts, you need to make you sure have the following things really bolted down:

1) Ideal Customer Profile: usually it helps to have a clear idea of what your target is, in order to define how you will be approaching them. The Ideal Customer Profile is a central document in informing both lead generation, your sales approach, and even building out your call scripts. This doesn’t mean you have to be 100% correct on it, right off the bat. This profile will be a living/breathing document through your company’s lifetime, and it is sure to evolve over time based on market feedback. Without some semblance of an understanding of who you are trying to get in front of, it will be impossible to build out your outbound efforts.

2) Sales Reps: make sure you have the right number of sales reps to handle the responses from your outbound campaigns. It might sound a little self-evident. But not having those resources in place will actually hurt you a ton. It’s one thing to generate responses from prospects through massive outbound. If you don’t have the reps to handle the engagement you’re getting at the top of the funnel, then your whole initiative is not only wasted, but your brand is hurt by it. Imagine being a prospect. You show an initial interest in a product or service — or at least it’s high level value propositions — only to be abandoned once you initially respond. In order to prevent this from happening, I recommend modeling out your outbound efforts before you even begin. From your model, you’ll be able to see how many introductory calls are generated per week and per month. Depending on your reps’ current workload, you’ll then be able to figure out if you have enough warm bodies to handle the responses from leads.

3) Sales Tools: your sales tech stack is going to be your friend throughout this process. You need to make sure you have the basics in place to meet the upcoming increase in demand. In other words, you’ll need a sturdy CRM (in most cases, I recommend these days), and email marketing software to manage your campaigns (I always recommend for those purposes).

4) Sales Interactions: it is imperative that you have had enough sales interactions with the market so that you have established a few things. One: you are going after the right market. You’ll know pretty quickly in your early sales interactions if folks are interested in what you’ve built. You’ll see them lean in, or hear their excitement over the phone. You’ll feel the pull from the market. Two: you have iterated enough on your Ideal Customer Profile so that you have a rough idea of who you are selling to. Three, you’ve been able to get some semblance of a sales process together.

5) Sales Process: it’s critical that you have a sales process that closes customers. Even if it’s just a couple of trial customers. The process doesn’t need to be optimized, or feel slick. It just needs to have gotten a handful of customers across the goal line. In other words, it just needs to work. Once you have such a method, you’ll feel confident in turning on the firehose that is outbound.

Test send your emails to several different email providers.

Make sure to test your emails by sending them to several email providers (Gmail, Yahoo, Outlook…) before launching your full-blown campaigns. It’s worth the hassle, and you would be surprised how emails might show up differently in different email inboxes. Some of these differences are due to formatting. To solve for this, you might start by removing any formatting before inputting it gradually. Particularly if you’ve cut and pasted something from another document initially.

Although this is sure to feel a bit tedious, you’ll be rewarded by having clean, professional emails delivered to your prospects time and time again. Prospects already have plenty of reasons to rebuff you when you cold email them. Removing any additional excuse not to engage with you will prove beneficial.

Leverage outbound for other channels.

Another non negligible advantage of outbound is that it enables you to test messaging very cheaply. Remember, you’re not paying for ads here, you’re just emailing/dialing up customers. Every interaction is an opportunity to test a new messaging hypothesis very cheaply and immediately. Compared to the cost of buying ads on Facebook or Google, dialing/emailing is cheap. At most, you’re paying a lead generation provider at $1 – $2 per lead and a small monthly fee for email software (I recommend

While ads broadcast very few messages to a broad audience, outbound allows for the testing of many different messages to different segments. On average, the same prospect will be hit by several different messages, when sending out email campaigns. Outbound also allows for a back-and-forth with the prospect, which enables you to zero in on what is and is not working.

That’s why I recommend doing outbound to my clients and other startups. And to do it early in your product release cycle. Once you’ve formed a clear idea as to what kind of messaging resonates with certain audiences, you can actually go ahead and leverage that know-how to your other channels, like ad buys or even PR.


Your email subject line is your pickup line.

Treat it as such. If you’re eyeing a potential mate across the bar, the only thing that matters is your ability to get their attention. Without a conversation starter, you have nothing. You could be the most scintillating conversationalist, the best listener, the most inquisitive mind, the most empathic person on god’s green earth, or the most gorgeous human being. The person whose attention you’re seeking might not find out. Unless you are able to start a conversation and engage with the apple of your eye.

The same applies to outbound. Unless you’re able to grab your prospect’s attention with your subject line, you can’t expound about your product’s benefits, or even ask for a 15-minute introductory call. Your opener earns you that opportunity.

I used to remember thinking along these lines, “Well, the email body has a lot more text in it, than the subject line. That gives me a lot more to work with to convince a prospect to respond to my email.”

Sure, it’s more characters to work with. But unless you get the prospect to actually open your email, thanks to a cleverly-worded subject line, your scintillating email body prose doesn’t even get read. It’s a total waste.

That’s why I recommend that my clients test and iterate on their subject lines early on in their outbound efforts. Without really nailing those, the email body doesn’t even matter. I usually suggest that we budget the first few weeks to really test out subject lines for the overall campaigns. Once we’re comfortable with our open rate — we usually aim to land at 40-50% — we can actually pull up our sleeves and get to work on the email body, whose goal is to get a prospect to respond.

Forget about your product or features. Tailor your message to showcase benefits to your prospect.

This is an age-old sales maxim. You are often told in sales to focus in on what value or benefit your product can deliver, when delivering a pitch or giving a demo.

This is further accentuated when you have a short amount of text to grab your audience’s attention and get them to engage with you. It’s important to lead with the benefit or value right off the bat: both in the email’s subject and body.

With outbound, you have the benefit of choosing your prospect. She has been targeted carefully: you have spent considerable time establishing an Ideal Customer Profile and sourcing the corresponding leads. Take full advantage of this targeting by tailoring your message to your prospect. The thing any good salesperson does is force themselves to walk in their prospect’s shoes.

If you really are able to do that, you’ll realize that the last thing you would ever want to receive is yet another email from a company touting their latest product, service, or feature. Your immediate reaction (and you’d be right) is, “What’s in it for me?” Unless you’re able to answer that question, with clear and succinct benefits/value for your prospect, there is a real chance their eyes will glaze over as they read your email and move on to the next one sitting in their inbox.

At some point in your email, you’ll have make your pitch — in just a few sentences — to entice your prospect. Make sure you do it in a way that is relevant to your target.

You may be tempted to lead with your product’s bells and whistles, like this:

“Our widget is great because it has X, Y, and Z features.”

Instead, adapt it to the decision-maker you are targeting, and tell her why it’s important to her.

“Our widget helps streamline your back-end infrastructure and reduces your overall IT costs. Our customers have seen their IT costs go down by at least 55% per year after integrating it.”

Notice that we transitioned from mentioning features that were part of the widget — a product centric approach — to actual solutions and demonstrated value for the prospect — a customer-centric approach. The dynamic is morphed: the prospect goes from feeling completely disconnected and unconcerned about the widget to immediately seeing value in it. It matters to her now. You’ve given her the “Why” she should care. And you have even sprinkled in some social proof for good measure. Customers have already been delivered the value. Why don’t you join their ranks and reduce your costs, too? Finally, adding metrics which you have already garnered — in our case a minimum cost reduction of 55% — adds a lot of credibility to your claims. It’s the impartial, indisputable data that supports your assertions.


Write to a friend.

It can be very tempting to expound on the benefits of your product or service in the first email. What you’ll lose when you do this, however, is your prospect’s full attention. They will get lost in a big email and tune you out.

Remember: your only goal with cold emails is to generate interest and book an initial introductory call. All of the selling doesn’t need to happen right then. All you need to do is pique the prospect’s interest and generate a favorable response from her.

With that in mind comes the following piece of advice, that was initially delivered to me by Conor. In giving me feedback on some email copy, he once told me, “Your email feels sales-y. You would never start an email to a friend like this. You would start with something like this….”

Hey Paul – I thought you’d be interested in hearing how the Best Buy of France {{insert stats}} with a cool new feature that tracks user behavior online and offline, right from the POS.

If you’re interested, let me know and I’ll send over more info about it.


The lesson was clear: make things less formal and more colloquial. I had made the mistake of being overly polite and formal. I had to be more direct and to the point. Since receiving Conor’s advice, my response rate has gone up substantially. My prospects must feel less sold to. And they must feel like I am getting to the point, with less throat clearing, nor exchanging unnecessary pleasantries.


Don’t be afraid to try far-out ideas.

Let’s face it: we are all bombarded by messages all day long. We’re pitched numerous products, and asked to respond to numerous branding messages. Impressions hit our retinas a record clip from sunrise to sunset. It’s a surprise our neurotransmitters aren’t completely shot by the time we get to our lunch hour on weekdays. To break through, it’s important to separate yourself from the pack. And at times, that means pushing the envelope a little bit.

I would highly encourage you be as creative as you can, and embracing as many crazy ideas as you can. As we’ve seen above, unless you engage with your prospect, there is no way to start a meaningful conversation. And as you’ll see, some of the zaniest ideas happen to be the most successful when it comes to outbound.

One of the most success emails we’ve ever sent out has been the simplest. It works so well that I have used it in virtually all outbound campaigns I have built since my former colleague Chris Fitzgerald suggested it when we were at Whitetruffle. It consists of making your first follow-up email in your email campaign —  usually your 2nd email — the following:

Subject Line: email


Did you get my email?


Yes, that simple. And the results are off-the-charts. It usually got us the best response rates of any email we would send out in campaigns that could be 6 or 7 emails long. It probably tugged at people’s need to not miss out on anything, while also removing any “pitching” from the conversation.

Sent from my iPhone

Another wild idea that I heard works really well is courtesy of Steli Efti and the folks at using the “Sent from my iPhone” at the bottom of your email copy. Much in the same line as making your emails plain text and unsophisticated from a graphical perspective, this removes all formality from the exchange and makes the email feel both personal and casual. Recipients feel they are getting something from an actual human being and not an automated email from a profit-driving corporation trying to create separation between them and their cash.  

This next idea was graciously contributed recently by my close friend Austin Gunter. As you’ll see from the email exchange (screenshot below), the sales rep from LeadGenius used a simple trick to get Austin’s attention. In one of his follow-up emails — more than likely in an automated email campaign — the rep actually pretends to have forgotten to send an important case study, and proceeds to email it over. This creates the illusion of spontaneity and humanity behind the message. Austin wasn’t yet another nameless prospect that was being bombarded by massive email campaigns. He had been precisely targeted and vetted as a worthy target for LeadGenius and a sales rep had taken the time to personally write him. When Austin asks him about his gimmick, the rep readily admits that it has proven successful at increasing response rates from prospects.

This next one came to me recently while working with a client. I had sent a response to an inbound lead requesting a quick introductory call. It had taken a while for us to address this lead — we had been flooded with inbound interest — and the prospect responded that they didn’t remember having entered their info in the online demo request form. He went on to ask me when and where he had entered the information. I responded with my client’s online demo request URL. To which the prospect responded that “either this was the most awesome outbound tactic ever or that I’ve completely forgot about reaching out.”

The prospect had forgotten he had reached out. But he served up a new outbound tactic idea. If you have an inbound online submission form, you can pretend like your outbound prospect had reached out initially. It will give the impression that you weren’t the one doing the cold outreach, but that your cold prospect was the one that had reached out. The prospect consequently feels invested in your cause and is most likely going to feel like they need to engage with you.

All of these ideas can be embraced and leveraged by sales and marketing teams. I usually encourage folks I work with to really push themselves creatively. We don’t usually censor ourselves in any way, until we have a good set of zany ideas to work with. Then, you can spend the time to scrutinize each idea and decide on whether or not it has legs. The other factor that must be evaluated is the comfort level of the team and company in employing certain tactics. I have seen companies that immediately feel uncomfortable when using any tactic that might feel like it’s on the edge. I have also worked with teams that have embraced the old Raiders’ motto of “Just Win, Baby”: they were ready to do a lot of things to get their foot in the door, and get conversations started. I am not here to make judgments. I think it’s important to highlight the tactics and ideas that have worked and let folks decide on whether or not they should utilize them.

With that said, I’d invite you to be as creative as possible when doing outbound. You’ll get rewarded for it. Prospects have gotten more calloused and desensitized about receiving messages from drip campaigns and automated email marketing. I had one prospect just a couple of days ago write back to me, “I’ll answer that if you prove you’re a real person”. If you spend the time being creative, you’ll find ways to appear more human in your interactions and get better engagement from your prospects. As you scale up your outbound sales, feel free to share some of your insights and ideas with us. You’re sure to land on some nuggets that will benefit us all.