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, ask 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.