Emailing Prospects

You’re reading an excerpt of Founding Sales: The Early-Stage Go-To-Market Handbook, a book by Pete Kazanjy. The most in-depth, tactical handbook ever written for early-stage B2B sales, it distills early sales first principles and teaches the skills required, from being a founder selling to being an early salesperson and a sales leader. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

​caution​Email is your friend. It is an extremely powerful means of directed outreach toward prospects, when done correctly. It has the benefit of a strong ecosystem of automation and instrumentation tools, benefiting from over a decade of innovation in the space. And it is especially powerful in conjunction with calling and voicemail delivery. But be careful. When done incorrectly, it can make you look like you have no idea what you’re doing and poison potential client relationships. Bad emails are one of the main reasons why sales gets a bad name. So let’s make sure to do it right, okay?

As covered in the previous chapters Early-Stage Sales Materials Basics and Early Prospecting, you need to have both a set of prospects (who have been prequalified) and their email addresses, along with a set of email templates that characterize why you think they have the business pain your solution solves, describe what you think you can do about it, and conclude with a call to action to engage in a one-to-one commercial conversation—the mythical demo we seek to arrange.

One email probably won’t be enough to get the appointment on the calendar. As much as we’d like to think our words are magical and our arguments breathtakingly compelling, it’s probably going to take more than one shot to gain a response from the prospect—which is why we have more than one email template! People don’t want to read a book dropped in their inbox (he says, while writing a book). Rather, they want quick snippets of information, hyper-targeted to them, providing them insight and value. You can achieve this through personalization, but also by breaking up your messaging into multiple distinct emails. Splitting up the buckets of your narrative into separate short emails, constrained to a single thought, can be a very effective way to drip messaging about the pain you’re addressing. With this approach, you can demonstrate that you sniffed out that the prospect has that pain,and that the reason you’re emailing is to verify this, help them solve it, and be a hero. It’s hard to do that in a single monolithic email. Think of it as akin to what flash sale sites like One Kings Lane, Gilt, and Groupon figured out with their daily emails: delivering targeted, relevant content, one bit at a time, over time, is a great way to drive a prospect to eventual conversion.

The key, of course, is to ensure that you’re not showing up in the prospect’s inbox like a carnival barker, with exclamation points every sentence, bombastic claims, and all sorts of HTML layout elements. Yuck. Instead, using conversational, calm, text-based messaging, demonstrate your focus on their challenges. These emails should have the tone and candor of a message from one CEO to another (even if it’s actually from a founder to the manager of a function within the target organization). Moreover, small, lightweight, chunked emails help you take advantage of modern email marketing tooling, like lightweight drip marketing, which we’ll tackle in a bit.

And as touched on in Early Prospecting, if you are able to determine a potential warm intro that is a connection (either via a social network or just working in the same org), there is a somewhat different protocol there, but which still relies on high quality templates and outreach that make a compelling argument to the target. It just happens that you have someone adding a reputation layer of, “He’s good and wouldn’t steer you wrong,” on top of your argument to the target contact.

Manual Email and Instrumentation

The most basic email outreach will be through your standard email client, whether Gmail or Outlook. This is the most laborious form of email outreach, and is fine to start, but at a minimum should involve email instrumentation via open and click tracking of the sort Yesware, Tout, and Sidekick by HubSpot provide. These tools embed a small, transparent pixel in each of your outbound emails, invisible to the recipient but which their email client (whether Gmail, Outlook, or mobile email) loads from a remote server on open. The result is that those tools know when your prospect opens that email, and can share that information with you. So too with links in your emails. These solutions will rewrite the hyperlinks in question, creating tracking hyperlinks unique to that specific email. So when the recipient of that email clicks on a link, routing through that tracked hyperlink on their way to the eventual target (your YouTube video), again, Yesware or Tout or whoever will see this action and can share it with you. Yes, it feels like the NSA. Get over it. It’ll help you close.

This is why I was jumping up and down about click targets in Early Prospecting. The more juicy hyperlinks (like links to video thumbnails or to infographics or whatever. I haven’t experimented with animated GIFs, but really want to.) are sitting in that email, enticing a click, the better. We care about this activity, because it shows that the prospect is interested in what you have to say. The more opens and clicks, potentially the more interest. If a prospect forwards your email to his team, and all of sudden you start seeing opens and clicks from different geographical locations (based on the IP addresses of the devices loading that pixel or clicking that link), even better! If he receives the email one day, opens and clicks on it, doesn’t respond, and then two days later opens it again (which Yesware sees, again, as the email client loads that pixel again), it shows you that he’s still thinking about what you had to say. He has a crush on your email. Fantastic! This tells us it’s a prime time to email him again. Or call him, which we’ll talk about more in a second.

This sort of email instrumentation is where there are benefits to lightweight CRMs like SalesforceIQ or Close.io, or SDR tools like SalesLoft and Outreach, which typically integrate Gmail or Exchange into the CRM. These products allow not only for easy templating (Yesware and company typically also have templating functionality), but also for open and click tracking that is baked right in (and they also record the outreach that has occurred).

Mass Mail and Drip Marketing

Nowadays, manually sent, instrumented email is table stakes. The next generation of email technology comes in the form of mass mailing and drip marketing. Brand-new Tesla versus mid-2000s Camaro. In drip marketing, which was pioneered via solutions like Marketo and Eloqua, individual email messages are dripped out to recipients over time, delivering snippets of messaging piecemeal and nurturing prospects, eventually driving them to conversion. Of course, this is relevant to sales as well as marketing, and so a number of software providers have stood up lightweight drip marketing solutions to assist sales staff. The notion of following up with prospects with whom you’re trying to set an appointment is a sales best practice, but historically, it’s been time-consuming to have to not only remember to do so but then manually go back to the thread in question, reply to it, and drop in new messaging. These modern drip-marketing solutions do this for you, with fresh content, so you’ll never have to send a dumb-as-nails, “Just following up on this…” message. And these solutions are smart enough that when prospects respond to you, they drop out of the drip.

These tools can be utilized a few different ways. The most basic is mass mailing with automated follow-ups. In this approach, you can load up a set of prospects and their relevant metadata, typically in the form of an excel or CSV file, which will then be fed through a series of templates that turn that data into customized outreach emails via mail merge fields. The results can be as basic as the awful mass mails that you’re used to receiving and likely never respond to, or these can be thoughtful and advanced, making use of the demand signifier metadata that we talked about in Early Prospecting—like the number of potential users in-house, a calculation of how much time or money is being wasted based on some ROI metric you’ve calculated, or links to parts of each prospect’s website. The latter requires smart prospecting and templating but will make your outreach that much more fruitful. The former makes you look stupid and irritates your prospects, so don’t do it. No one likes the person who drives their Tesla into a wall.

An even more advanced approach involves a first outreach email that is heavily manually personalized—in addition to having basic merge fields like {!NAME}, {!COMPANY}, {!NUMBER_RECRUITERS}, {!CRM_TYPE}, {!NUMBER_PAGEVIEWS}, or what have you, you might include screenshots or custom recordings as discussed above. Or some sort of opening pleasantry that indicates a real human looked to see that they went to the University of Alabama, and that, wow, the Crimson Tide look particularly fearsome this year, and boy, what is up with Nick Saban’s hair? Or all of the above. In studies, the drip-marketing vendor Outreach has seen response rates for human-customized emails go as high as 12% for an initial outreach, as compared to 5% for a baseline of totally unpersonalized outreach. I like to call this a “single-serving” drip-marketing campaign (or maybe a “pour-over” campaign?), where you can invest five minutes up front to knock an email out of the park.

While this level of customization executed for each in a series of messages would be overkill and totally inefficient, drip-marketing tooling lets you leverage that initial investment each time the system replies. Even if the prospect doesn’t respond, the incremental drip emails will reply to that same email thread. That will give you the benefit of increased open rates, as prospects are more likely to open replies (believing that they are already participating in the thread). Moreover, as your excellently written and targeted messages show up to the prospect, she will be able to easily scroll up to the top of the thread, or look down at the quoted prior emails, to see the background, along with your initial customized outreach. In effect, your incremental emails are driving the prospect to read that first email (and, of course, the ensuing ones). So your initial five-minute investment gets leveraged at each step of the drip program. (Different vendors have this implemented differently, so make sure to double-check—Outreach in particular focuses on this approach.)

In the graph below, you can see the responsiveness over time in drip campaigns featuring varying levels of personalization (and compared to a one-and-done email outreach—ugh, the horror).

Figure: Drip Campaign Responsiveness Based on Level of Personalization

Source: TalentBin

Human-personalized initial outreach, when levered across a seven-email drip campaign, results in 30% more responses than a drip campaign with only heavy auto-personalization, and nearly 50% more responses than a drip campaign with a lightly customized first email. And 15x the responses of the one-and-done approach. If you’re thinking, “Wow, it’s kind of a no-brainer to adopt this approach, Pete,” you’re thinking about it correctly.

Here’s that same data represented another way. Check out the differences in response counts for a 100-person campaign based on different personalization approaches.

Figure: Response Counts Based on Different Personalization Approaches

Source: TalentBin

A last point about customization and context relates to social context. In the age of LinkedIn, Facebook, and Twitter, it’s fairly easy to get instantaneous context that can help demonstrate to the prospect that you’ve done a good job qualifying her (above and beyond the business pain context that we’ve already talked about). That context builds rapport, and raises the likelihood of setting the appointment. This can mean looking at things like a prospect’s prior companies (did she work somewhere you worked before?), your shared LinkedIn or Facebook connections (is there someone you both know that you can use to break the ice?), or her Twitter profile (can you refer to something she tweeted recently that is fun or interesting?). This is why I like prospecting staff to grab prospects’ LinkedIn profile URLs for quick and easy reference. Nick Saban’s hair, a tweet about how bad the Giants are sucking, or a prospect’s post about looking forward to a margarita after work—all are fair game and will help drive responses.

From a timing perspective, be thoughtful about when you want these email campaigns to fire. People get a lot of email these days, especially decision-makers who are desirable targets for many solution providers. So in addition to being awesome and personalized, your content needs to show up at a time that makes sense. Typically this means avoiding Monday mornings, when prospects will have big fat inboxes full of stuff to quickly triage. Target times when your email may be looked at as infotainment: 10 a.m. on a Tuesday, when they have likely cleared out those inboxes, or 6 a.m. or 7 a.m., when it might be the first thing they see on their phones while riding the bus, or even after office hours, like 7 p.m. or 8 p.m. Essentially, think about low-traffic times when your email will stand out as the delightful diamond of commercial wisdom that it is!

There are a number of solutions that provide this functionality with variations on the theme. Outreach, Salesloft, PersistIQ, MixMax, Sendbloom, and others are all focused primarily on this lightweight drip-marketing functionality, while Yesware and Tout have some partial functionality in this regard but aren’t as developed. I highly recommend making use of one of these solutions to raise the volume of targeted, relevant outreach that you are able to execute as a single person—it’s like having your own personal robot Market Development Rep before you staff that role.

Before we leave this section, a note on drip marketing and spam. A lot of non-sales staff see this sort of thing and think, “My goodness, that sounds like spam!” They can be forgiven for this attitude, given that they’ve probably received large amounts of rubbish, untargeted outreach from lousy salespeople in their time. But that doesn’t mean that you should forego a perfectly good tool because someone else has used it poorly. As noted in Early Prospecting, if you have done a good job of targeting prospects who are very likely to have the business pain you resolve, they will welcome your outreach. If your messaging is clear, straightforward, non-bombastic, and focused on them—with each communication adding value to their lives by teaching them something they didn’t know, or offering a way of solving a problem that’s been frustrating them—your outreach will be welcomed with open arms.

As a matter of fact, as seen above, the highest response rate to cold outreach emails, based on data from an Outreach study, is to the second email in your drip campaign (18% compared to 12% for first outreach). Response rates then hold steady (17%, 17%, 13%) through the fifth outreach, at which point they start to decline. In fact, by adding an, “Okay, I’m breaking up with you” type email to the end of your drip campaign, you can actually prompt prospects to act. They’re used to sales reps continuing to follow up ad infinitum, so they feel that they always have the option to respond to you later. If you specifically say, “I’m not going to email you anymore, but I have conviction that this is relevant to you and will make you more successful in what you do,” it can force a prospect to actually consider your arguments and, ideally, respond. These approaches work so well because prospects are simply used to terrible, irrelevant, one-and-done outreach from sales reps. They ignore the first outreach—but by sending a second, third, and fourth, and by making sure that those messages are relevant, you can sprint past all those other terrible sales staff.

But the onus is on you to do the work up front to make sure that your prospecting has been sound, your messaging is relevant to those well-prospected contacts, and you’ve structured your prospecting data in a way to make great use of sales technologies. It’s not the tool that makes it spam. It’s the person using it wrong that does.