From “Founding Sales: Sales for founders (and others) in first-time sales roles” by Pete Kazanjy founder of Atrium Sales Analytics. Follow Pete on Twitter and LinkedIn.
Consider checking out How to Use This Book and Who This Book Is For sections to start.
Introduction
Now that you’ve got your list of highly targeted potential accounts, and associated points of contact, it’s time to tackle the business of actually selling. You were probably wondering when we’d get around to that! Up until this point, we’ve mainly been dealing with tooling to enable you to sell. But as covered in the Sales Mindset Changes chapter, the best tooling in the world is useless without the actual activity of emailing, calling, presenting, demoing, and closing. That’s where the true work of “selling” is done, and because of this, it’s often the scariest to people who have never done it before. They believe deep down, secretly, that planning and planning, building more and more tools, can shield them from potential rejection. But experienced salespeople know, in the words of the great American philosopher Mike Tyson, that “everyone has a plan until they get punched in the mouth.” Sure, getting punched in the mouth is no fun, but you can’t win if you don’t get in the ring. Let’s smile and get ready!
What we’ll cover in the following chapters will prepare you for the various motions of selling, from appointment setting to “pitching” via sales presentation and product demonstration, all the way through closing and pipeline management. Note, though, that simply reading about these actions isn’t enough, and you should not expect to be naturally comfortable with, and excellent at, any of them. It will take practice and many repetitions before you have your pitch nailed and are eminently comfortable with all the objections prospects will throw at you. But this is totally to be expected, and the best way to get to that point is to just start!
Stages of the Sales Cycle
I like to think of the sales cycle bucketed into several major stages: First, there’s “outreach and engagement,” where you’re engaging a prospect account with the goal of setting an appointment. Next comes “pitching,” where you begin a commercial conversation with a prospect with the goal of eliciting more information about the particulars of their situation and persuading them that your solution fits their pain. And the stages continue all the way to “closing,” getting the prospect to sign on the line that is dotted, and the associated pipeline management. Each stage has it own set of actions, and it own goals, which we’ll cover in depth.
Importantly, you will be the one taking all of these actions. This is another place where early-stage founders get tripped up. They hope that they can just “hire a sales guy” who will figure this all out. Go to Costco, buy a bin of sales dust. Sprinkle some sales dust on product. Poof: IPO. This is simply not the case. Sales professionals are adept at taking a proven product to market with a proven message and a proven set of materials—with minimal variation. They are not there to prove those things out on their own. The selling you will be engaged in is what is known as “evangelical sales,” a mix of product management, product marketing, and sales. In evangelical sales, there is a tight feedback loop between your interactions with the prospect and modifications of both the selling materials (product marketing) and even the features of the product itself (product management). It will be an iterative approach, with a number of false starts. But that tight feedback loop is indispensable in tuning your go-to-market in a way that allows you to start winning customers and, later, to package your approach in a way that can be replicated by an army of sales professionals. But the only way you’ll get there later is by doing it yourself now.
In this chapter, we’re going to touch on the first part of that cycle, “outreach and engagement,” with the goal of getting appointments on your calendar. A little later, we’ll cover the mechanics of presenting to a prospect, demoing, and then working the deal as it moves down the funnel. Both are important, in that if you don’t do the first, you won’t have the opportunity for the second. And even if you’re somehow amazing at closing business from the first step, if you aren’t able to reliably fill the top of your funnel, you’ll struggle to acquire the number of customers you’d prefer. A .500 batter who only gets a single at-bat a game isn’t nearly as productive as one who has three or four a game. So let’s make sure you’re getting those at-bats.
Setting Yourself up for Success
As noted above, there is a particular tempo to enterprise sales’ distinct stages. In this first stage, the goal is to set up a commercial conversation about the prospect’s business pains and how your solution could potentially solve them, a.k.a. a “pitch” or “demo.” The goal at this stage is not to sell the solution. You’re simply “selling” a conversation—the opportunity to learn more, and tell more. The same way that the goal of a first date is not to get married, but rather to get to a second date (assuming there is a potential fit!). You try to get married on the first date, it’s gonna be an awkward scene. Same with sales.
As a non-sales person approaching this, you have an advantage of sorts over pure sales professionals seeking to set appointments. That is, because your offering is early stage, and you are not a salesperson, you can often approach these conversations as “research” or “customer development”—trying to understand pain points, and how they are currently solved. There is a balance here, as it is important to make sure that these conversations always remain in the realm of the commercial; you don’t want prospects thinking this conversation has nothing to do with addressing their business pains and potentially solving them, for a price. But because you’re the founder, CTO, CEO, or what have you, you can use that to your advantage, and in doing so reduce the friction of getting these meetings on the calendar.
Management and Early CRM
Given the activity-centric nature of sales, you’re going to have many balls in the air concurrently. As noted in the Sales Mindset Changes chapter, this is a new experience for most professionals. And while you may be used to being able to keep all your open items and projects “in your head,” this is extraordinarily challenging to do in sales. Every potential conversation, every conversation that is in flight, and all previous interactions are simply too much for someone to remember at once. Yes, yes, I’m sure you’re very smart and clever, but there’s no way you can keep it all straight in your head. And if you can, you’re not dealing with enough prospects concurrently! This is why modern sales organizations rely on customer relationship management (CRM) software to handle this issue—not only to help reps keep track of things, but to support management functions too, like activity reporting, win-rate tracking, and even financial reporting on how many deals are happening.
For a sole founder, I’m split on the necessity of using a full-blown CRM to start. As someone who is extremely persnickety about these things, but also now quite adept at Salesforce CRM (the industry’s CRM of choice), I would always use Salesforce. It’s the default sales system of record (a distant second being Microsoft Dynamics), but with the power and extensibility of the tool comes a fair level of complexity and configuration requirements. For someone just starting out, it could be overkill. Given the small scale of your initial set of prospects, you could potentially get by with a Google Sheet, where each prospect is represented by a row, with a column for various pieces of deal-state metadata (as we talked about in the Prospecting chapter). A middle ground would be to use a “beginner CRM,” like a Pipedrive, Close.io, Insightly, or Hubspot CRM. While not as powerful as Salesforce, and lacking the broad partner ecosystem of third-party tools, these products can be helpful in providing more structure around tracking who you’ve engaged with, who you haven’t yet, and who is in what state. Regardless of whatever claims are made by marketing teams, the purpose of the CRM is to help you keep straight who you’ve talked to, and to capture those communications (via email or notes from calls).
However, you should know that none of those beginner CRMs will scale for the longer term. Eventually, you’ll end up on Salesforce.com; it’s just a question of when it will happen. How’s that for a nice market position to be in, eh? Maybe you’ll get your solution there eventually.
Materials and Personalization
We touched on materials in the previous chapter, but to recap, you’ll need your set of prospects, the relevant pieces of metadata about their demand indicators that you researched (e.g., number of recruiters, number of open jobs, site traffic, etc.), a set of outreach emails with supporting collateral (i.e., video demos), ideally split up into a series of emails that can be dripped out over time, and your phone script.
The more you can demonstrate prior research and personalization, the better response you’ll have from would-be prospects, who are used to irrelevant and poorly researched blanket outreach from crappy sales staff. By pulling relevant pieces of metadata into separate data fields for each of your prospects, you can get the best of both worlds: the automation leverage of mail-merged and drip-marketed email outreach along with extremely customized demand indicators and messaging. Other ways you can make your outreach more impactful include screenshots or little demo videos (Jing is great for this) that are customized for the prospect in question. Shoot, as you record that lightweight video, you can even speak over it like you’re talking to your prospect—a form of “video voice mail/email” if you will. Who doesn’t like it when someone makes them a personalized love letter?
Emailing
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 voice mail 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 Sales Materials and Prospecting, you should 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. We talked about this in the Sales Materials chapter, but splitting up the buckets of your narrative into separate, short emails, constrained to “one 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 “CEO” 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 the prospecting and materials chapter, 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 a good guy 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 (i.e., 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 the Sales Materials chapter. 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…” And these solutions are smart enough that when prospects responds 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 customize outreach emails via mail merge fields. The results can be as basic as the crappy 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 the Prospecting chapter—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 guy who drives his 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” (is that 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). 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:
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”: 10am on a Tuesday, when they have likely cleared out those inboxes, or 6am or 7am, when it might be the first thing they see on their phones while riding the bus, or even after office hours, like 7pm or 8pm. 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 Touthave 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 bullshit, untargeted outreach from crappy 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 our Prospecting chapter, 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. That is, 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.
Calling
Cold-calling is the epitome of everything that scares first-time sales staff. While not face-to-face exactly, it’s a synchronous interaction with the very person who can reject your solution, which, of course, your own personal worth is pretty heavily tied to. Why would I possibly want to put myself in a situation where someone could stomp on my product and, by extension, me? For a lot of reasons, actually. Because synchronous verbal communication, miraculously, is a really rich way of communicating and gathering information. It’s almost like it might be one of the linchpins of the last few hundred thousand years of human evolution!
The trick to calling on your prospects, unsurprisingly, is similar to the trick to engendering email responsiveness: make sure that your solution is relevant to their situation, get your point across with clear messaging, and demonstrate that you are concerned about their situation with a customized, prospect-centric approach.
So let’s shed that fear of cold-calling right now. Yes, it will take some getting used to. But remember, you’re calling highly qualified contacts who have the problem you solve, and you’re seeking to help them solve that problem. Who wouldn’t welcome that?
Attempting Contact
Call Timing
The success of your phone outreach will often be contingent on the times at which you call. Connect rates can vary substantially depending on the day-in, day-out tempo of your prospects, so being in tune with this is helpful. For instance, if you’re calling on white-collar office workers (say you’re a recruiting or sales solution and are calling on Directors of Sales Operations or VPs of Talent Acquisition), then your better bets are going to be early in the morning, just as people are getting into the office, or at the end of the day. Middle of the day is tougher because people are away from their desks, in meetings, and going to or coming from lunch. Another trick can be particularly late calling. If you want to avoid gatekeepers, and get directly to a senior executive, often they are still around at 6pm or 7pm, when executive assistants have gone home.
If you’re calling on small businesses, these times may be totally different. For instance, if you sell to restaurants, calling in the middle of service is a great way to piss off your potential customer! Figure out when your decision-maker’s day begins (maybe it’s 9am or 10am if they serve lunch, or maybe it’s the 2pm or 3pm doldrums between lunch and dinner service). Because all of your customers (assuming they conform to a similar profile) will likely share this cyclicality, when you get to the point of calling against customers in multiple time zones, you can prioritize the ones whose time zone is within the raised connect-rate interval, and follow the “10am hour” as it moves from eastern to central to mountain to Pacific time. Think about what the right “day cycle” timing is and target your calling then. Otherwise the proportion of your calls that result in connects will suffer.
Context-Sensitive Timing
As discussed earlier, email instrumentation via Yesware, Tout, Outreach, and others can be particularly helpful in making your calling more effective by showing you which of your prospects have been engaging with your outreach, so you can focus your calling efforts on them.
For instance, if a drip-marketing email fires on a Tuesday at 10am, you can prioritize your Wednesday morning calling based on who opened and clicked links in that email. At a minimum, those who opened and clicked will have context for your call, and they will likely be more receptive to your messaging.
Even better are calls and follow-up emails that happen in immediate response to opens and clicks. If you’re at your machine, and you see that a prospect just opened your email, give them a quick call. It does wonders for connect rates. This is where mobile sales email tools like Immediately can be especially helpful, in that you can see who has opened your email even if you’re away from your computer, and call them right away.
Point-of-Contact Discovery
Calling can be particularly useful when it’s not possible to get ahold of the email address of the most relevant point of contact for a given account, or if a specific point of contact wasn’t readily discoverable. (SMBs, like local restaurants, auto repair shops, etc., often fall into this category.) But when calling on these types of businesses, without a specific point of contact, the first step of your engagement will likely be to locate that decision-maker, as he may not be the one answering the phone. This adds a wrinkle to the messaging in your phone scripting; now you need to sell this intermediary, this gatekeeper, on why it’s a good idea for him to share the name of the decision-maker in question. Your best approach here is to use very, very simple statements of the value of your product, so someone who isn’t necessarily invested with authority can quickly parse them and realize, “Hey, it’s probably a good thing if I let Bob know about this.” (For example, if you’re Groupon, you might say, “Hi there! I’d like to be in touch with the owner, because I’d like to discuss how Groupon can make him twenty thousand dollars in one day. Who’s the right person to talk to?”) The goal is to make it clear to the gatekeeper that by helping you engage with the right person, he will be looked upon as a hero by the eventual decision-maker, likely his superior—and that if he doesn’t, that same superior will be upset to have missed this opportunity.
Unfortunately, doing decision-maker discovery via calling can be a game of cat and mouse (even if you’re Groupon!), which is why the prospecting approaches we’ve discussed are so helpful in shortening this exercise. And this is why solutions attacking the SMB market (like Groupon, Yelp, FreshBooks, etc.), where decision-maker identification (or even account sourcing) can be a challenge, will often rely on inbound marketing approaches of the sort HubSpot has heavily popularized. However, if there are no better ways to do so, you can call into these accounts, and seek to piece together who the relevant contact might be by asking who makes decisions about technology investment (even just getting a name is the first step), when she’s typically in the office, and if you can get her email address or direct phone number. You might be wondering who would give out that sort of contact information, but you’d be amazed what you can get by just asking. Especially in conjunction with a solid gatekeeper pitch (like the Groupon example above) that convinces the person on the other end that she’ll be a hero for bringing your solution to the fore (or potentially in the doghouse if she doesn’t). No one wants to be responsible for barring a valuable solution, so gatekeepers are often happy passing you off so you can engage directly.
Gatekeepers and Directories
Link to section
If you make contact with a gatekeeper, and you already know which point of contact you’re seeking to engage, a different set of approaches is required. In this case, you’re likely calling into the main switchboard. If there’s a dial-by-name directory, you may be in luck and able to go straight to the desk line. Of course, there’s a challenge there too: who answers their desk line nowadays? However, if you are able to get to the desk line, you may be able to connect to the target point of contact or, at worst, leave a voice mail. More on this later.
If there isn't a dial-by-name directory, and a human gatekeeper receives those switchboard calls, he’s likely pretty used to receiving calls from sales professionals. In that case, it’s good to just ask for the point of contact by name: “Hi there! Can you connect me to Frank?” If the organization is small enough that there is only one Frank, using just the first name will sometimes pass muster. “Ah, he knows Frank.” In larger orgs, it may be more of a challenge, as you’d have to specify first and last name, which does away with that approach. That’s fine: if the gatekeeper wants to guard the gate, that’s his prerogative. And honestly, that’s what he’s there for—to make sure that decision-maker time is guarded for things that are actually relevant. Conveniently, you’re only calling to discuss something that is relevant, so truth is on your side. It’s just a question of making that clear. You’ll likely get “Is he expecting your call?” Lying won’t benefit you, nor will being unpleasant to gatekeepers. They deal with pushy sales reps (who may have done poor prospecting and be approaching with an irrelevant pitch) all day long, so you can really differentiate yourself by being pleasant, cheerful, and respectful. Plus, it’s good karma. Deliver the gatekeeper the same shortened pitch about why your offering is relevant to Frank (“Twenty thousand in a single day. Sounds great, right? I want to get ten minutes on Frank’s calendar to discuss.”), and why he’ll be a hero for letting you through. If he’s not biting, you can always ask to leave Frank a voice mail, which the gatekeeper will typically be happy to facilitate (he doesn’t like shooting you down, either). If he’s willing to put you through (with or without a pitch), it’s also good to ask for the direct number for future reference: “Hey, can I get Frank’s direct line in case I get disconnected, so I don’t have to bother you again? Thanks!”
Voice Mails
Generally speaking, when you call, you’re probably not going to connect with the person you’re seeking to engage, which can feel pretty inefficient. That’s why calling is often more like verbal email (via voice mail) than anything else. In the Sales Materials chapter, we spoke to voice mail templates. Short and sweet and loaded with personalization related to the research you’ve done on the prospect, the magnitude of business pain you think they have, the potential benefit of talking with you, and the fact that you’re the founder of the company, seeking to learn. Of course you should leave your contact information, though it’s not going to be super common for prospects to return your call. Returning calls is a huge pain compared to just hitting “reply” in an email, which, again, makes voice mail behave more like audio email than anything else. Speaking of which, it’s more and more common for folks to have their work voice mail set up in a way that forwards an audio message (and maybe even a transcription) to their email. So think about your voice mail being consumed in that format.
There are other sneaky approaches to voice mail, like not actually leaving much context, and instead saying something along the lines of “Hey, Frank, this is Pete. Call me back. 650-892-4475.” Or even skeezier, “Hey, this is Pete returning your call. Call me back at 650-892-4475.” (That last one is like adding a fake “Re:” prefix on emails, to trick the prospect into thinking he’s already participating in a back-and-forth). While this sort of thing can be employed by market development staff, it’s a little more advanced than you probably need to implement. Instead, the straightforward voice mail, patterned after your outreach emails, is probably your best bet. And importantly, always use voice mail in conjunction with email; if your voice mail is well formed, and well delivered, it may inspire your prospect to simply hit “reply” on the email that came in at the same time.
Live Messages
Lastly, there may be occasions when the gatekeeper offers to take down a “live message” for the point of contact—that is, write down your information and share it with Frank. This is typically not a great idea, in that the transmission of information here will end up looking like a kindergarten game of “telephone.” Of course, you don’t want to tell the gatekeeper that you have little confidence that he’ll be able to pass along your message appropriately. A good approach is to instead frame it as a benefit to him for you to present the message yourself. Something along the lines of “That’s so nice of you! It’s kind of involved. Would you be open to sharing Frank’s email address with me so I can just send it to him directly?” If that fails, often the gatekeeper will be willing to share his own email address as an intermediary, which you can then email with an amazing, super personalized first-outreach email (instrumented with Yesware, etc. so you can see when Frank opens it). Of course, if you have Frank’s email address already, this isn’t necessary; instead, it’s a better idea to ask to be passed along to his voice mail. Or, you can try for the best of both worlds: “You know, it’s kind of involved. How about this: Just note that Pete called and wants to discuss how to make your business twenty thousand dollars in a day—here’s my phone number—and that the details are in his voice mail. And then you can patch me through to his voice mail. That saves you a bunch of scribbling.” Or something to this effect.
Making Contact
Because live-connect rates are so low, it can often come as a surprise when you actually reach your prospect. Like, “Whoa! Why did you pick up the phone?!” In this context, you have about thirty seconds to sell her on an appointment, using the framework you put in place in your phone script. The most important thing to remember is that you’re not selling the product on this call. You’re selling the opportunity to spend a limited amount of time to understand the prospect’s pains better, help her learn something new and valuable, and potentially solve a big issue she has. You would like to get on her calendar for ten to twenty minutes in the near future.
If you’ve been doing a good job with your email-based outreach, ideally the person on the other end of the phone has context on who you are and what it is you’re up to. However, by no means can you rely on that to be the case—these folks get a lot of emails, and it’s likely that yours, regardless of how well personalized and excellently and concisely written, have been going straight to their archives.
Once you deliver your scripted pitch, typically the response will fall into one of three buckets: success, outright rejection, and something in the middle, involving various types of objections—that is, not an outright rejection, but not agreement either.
Success
If your excellent prospecting research, coupled with compelling phone messaging, piques the prospect’s interest and she agrees to a follow-up call at a more convenient time, you’ve won. That was the immediate goal, and you did it. High five!
However, in your excitement, don’t forget to get all the info you need before you get off the phone. First and foremost is calendar availability. Don’t rely on scheduling over email; this is a rookie error—being so excited (or scared) that you pull a “Great, I’ll email you some times that could work!” That turns into email hell, and you just blew that demo you set. Instead, the approach should be “Wonderful! Are you in front of your calendar? I have availability on Thursday and Friday morning, if that could work for you. It would be best for us to block thirty minutes of time. Excellent, I’ll send you a meeting invite for that time with the relevant details in it. Make sure you accept it when it comes through so I know that time works and the appointment gets on your calendar. Thanks so much. I’m excited to talk more about this with you!” Make sure that you’re not setting the appointment too far in advance; anything over a week out heavily degrades attendance rates. Usually a good time frame is a couple days out; that raises the likelihood that the prospect will have an opening, but reduces the lag in which excitement can temper, lowering attendance rates.
Beyond calendaring, this is also the opportunity to get an email address, direct phone, mobile phone, or other pieces of contact information that you might need. (This is not the time for full discovery, though. We’ll get into that in the “pitching” chapter.) If you didn’t yet have the prospect’s email address, you’ll definitely need it to send a meeting invite, and it’s also useful for sending a reminder email ahead of the meeting. And if the prospect doesn’t make the meeting, you’re going to want to have a direct phone number to call and remind her, or to follow up after the fact and get the meeting back on the calendar.
Lastly, this is an opportunity to potentially involve others in the call beyond the individual point of contact you’re addressing. Again, you should be targeting the relevant decision-maker that you sniffed out during prospecting, but oftentimes if you have sufficiently excited the decision-maker you can pull in potential users, or influencers. For instance, if you connected with the VP of Sales and she’s excited to learn more, but you know that there’s a Sales Operations Lead and a couple of Sales Managers at the company, you could ask if the decision-maker would like them included in the call. If so, gather their contact information, primarily email, to put them on the meeting invite.
Hot Transfers
In rarer cases, the prospect may actually want to do the demo then and there: “Well, I have time right now. How about now?” If you were surprised to connect to your prospect, this one will probably really knock you off kilter! In sales land, this is known as a “hot transfer,” and it’s both fairly rare and a two-edged sword. On the one hand, it’s great that the prospect is so interested in what you’re doing and how you’ve described it that she’s open to spending thirty minutes with you then and there, and you certainly don’t want to say no to her on that count! On the other hand, you likely didn’t do all the pre-call planning that you would ahead of a scheduled demo, so your level of personalization and preparation may be wanting. But this doesn’t mean that you should do deep pre-call planning ahead of each cold call, thinking that you might end up in a hot transfer situation. No way! Most of the time you’re not going to connect, so all that prep time would be hugely wasted. Rather, the approach I like here is to proceed with the hot transfer demo, but treat this as a “demo lite.” Use the time to do your relevant discovery, and to offer a preview of what a fuller meeting might be, as a means by which to “sell” a full demo for which you’re able to better prepare. Set that expectation ahead of time by noting what you would typically do for a full demo (more on that later), and what you’re going to do here. In this manner, you can capitalize on the prospect’s immediate interest and availability, while lessening the impact of the preparation deficit.
Rejection
If you follow the prospecting and messaging instruction we’ve already covered, the amount of out-and-out rejection you encounter shouldn’t be terribly high. Prospects don’t like to completely close the door on something, but rather prefer the “not now” approach to forestalling decision-making (even if it’s the tiny decision of putting a meeting on the calendar!).
If you are seeing a bunch of out-and-out rejection, you may not be getting your point across, you may be targeting prospects poorly, or some other issue. In that case, listen for patterns of objection in your interactions that can help you proactively avoid these rejections. For instance, at TalentBin, recruiters and heads of talent were so used to being cold-called by agency recruiters that whenever they heard something with the word “talent” in it, they immediately thought “agency recruiter, reject.” We got to the point where we might start a call with “I’m not calling from a recruiting agency, so let’s just get that out of the way up front!”—which had the added benefit of adding some disarming humor to the call. If you’re commonly hearing a standard type of rejection, see if you can take a similar proactive approach.
With that said, you will certainly encounter rejection when you catch someone on a bad day and they’re not interested in hearing anything. But there are ways of turning those interactions to your advantage to “win the call”—that is, make progress in pushing the prospect down the path to becoming a customer, even if it’s the littlest step.
Firstly, you shouldn’t take rejections as “never,” but rather as “not now.” If you think about every massive company out there, the Salesforces, LinkedIns, and others, there were thousands of prospects who rejected initial outreach and eventually became happy customers. When you encounter out-and-out aggressive rejection, treat it as an opportunity to make sure your goal is understood and give the prospect another chance to soften: “Okay, I understand. It sounds like this is something that might not be a priority right now. My only goal was to seek to understand your business pain (good to specify it, like “how your technical hiring efforts are going” or “how your organization currently handles backdoor hires and missed fees”) and see how we can help with a fifteen-minute scheduled call. I know that you weren’t expecting my call, but are you sure you wouldn’t be open to a conversation at a more appropriate time?” If this gambit doesn’t work, then it’s fine to retreat to fight another day, typically in the form of “I understand. While I’m confident that we may be able to help your organization be more effective, we can table this for now. It will be my responsibility to be in touch at a more appropriate time.” This is probably in stark contrast to what you want to do, which is say, “Fine! Continue living in the dark ages and wasting time and money on the dumb way you’re currently doing things.” Yeah. Don’t do that, regardless of how satisfying it might feel.
This approach achieves a couple things. First, while you acquiesce to the prospect’s request to disengage, you’re doing it on your terms, stating your conviction that this is something that is highly likely to be relevant and helpful to him, and you provide him an “out” in the event he changes his tune. Further, you’re characterizing this as something that is inevitable. That is, “I’m not going to give up. I believe this is relevant to you, so you’re going to have to evaluate this on the merits, rather than dismissing it out of hand.” This characterization of inevitability—“I’ll be back” in the words our friend Arnold—sets the prospect up to be more attuned to your future emails and calls.
After disengaging from the call, you should absolutely send a follow-up email. It should be a subtle variation of your initial outreach messaging, crossed with some of the conciliatory messaging you used in your call retreat (templated, of course—“Rejected Call Template” sounds like a good title to me!). Thank them for their time and characterize why you thought your solution was relevant, with metrics supporting what you think it could do for the organization. Then close with a call to action to get something on the calendar (you’re still selling the demo at this point, even though you retreated from the call), along with a statement echoing that you look forward to being in touch in the future. Following up with the prospect like this gives him an opportunity to marinate on what you spoke about on the phone, and take that “out” you gave him to actually get something on the calendar. You’d be amazed how many people who seemed hell-bent on getting off the phone change their tune, and decide that they’d like to get on that demo after all, when delivered this sort of follow-up. It’s not luck. It’s that your call cut through the noise, followed by a little bit of footwork to capitalize on the focus you engendered.
Objection
The vast majority of your interactions will fall in between the extremes of success and outright rejection. And typically they will involve objections to setting an appointment. Your job here is to handle those objections—to help the prospect understand why his concern, while valid, is unfounded in this case—and drive to setting the appointment. The last thing you should do in the face of objections is comply, and disengage, as tempting as it may be to get out of an awkward, conflicted situation. This is just where the fun begins! In fact, rather than problematic, objections are great. They mean that your prospect is engaged, and at least thinking about the problem you’re addressing. They’re giving you a chance to make a better case. Every time the prospect raises an objection, it’s an opportunity to ask more questions and engage in a better conversation about their situation, and where your solution can potentially help.
The problem with preparing you for these objections is that they’re going to be specific to your solution’s space. Sales-productivity solutions will have different objections from recruitment-branding solutions, which will even have different objections from passive-candidate recruiting solutions. So you’ll just have to discover them as you go. But, importantly, you need to make sure that you are recording the objections you hear, and your responses to them. That will ensure that as you encounter them more in the future, you are able to handle them with ease—and later, when you hire staff to help parallelize your efforts, you’ll already have done the hard work for them.
With that said, there are some standard objections that people will use to try to get off the phone with you. If you’re prepared for them, you’ll be better positioned to get that meeting on the calendar.
“Call me later.”
This is typically a gambit to get off the phone without having to actually tell you “no.” Variants are things like “Can you call me in a quarter?” The problem with this is that if you comply, when it comes time to call the prospect in a quarter, what do you think his response will be? That’s right. “Call me in a quarter.” You can guess where this ends up. Now extend this across other prospects with this objection. Your end game becomes no demos, ever.
So rather than complying immediately, it’s better to flip it around on him. “I’d be happy to do that. But if possible, maybe we could spend thirty seconds right now to make sure that this is relevant to you. And if it’s not, in a quarter, I won’t unnecessarily bug you, and you won’t have to deal with irrelevant outreach. Great, right?” Then proceed with some lightweight discovery and qualification questions. Given that you’ve done a good job prospecting, and you know this prospect’s pain points, you should be able to build a good case quickly for getting a demo on the calendar.
The key to this interaction is a small negotiation trade-off. Instead of getting off the phone immediately, you held out the carrot of never having to hear from you again, which the prospect “bought” by giving you thirty seconds. And then it’s on you to blow him away with your research and messaging.
“I don’t have budget.”
This is tricky. We talked about demand-characteristic qualification in the Prospecting chapter, but we haven’t talked about budget qualification yet; we’ll do that more when we discuss discovery questions and pitching. The short of it is that it’s a good thing to know that a prospect has money to spend on a solution and knows what the process is for procuring that solution. If an organization truly has no ability to pay for things, it’s not a good use of time to pitch them, which is why budget is the B in the “BANT” qualification framework (budget, authority, need, timeline).
With that said, it’s highly unlikely that the speaker of this objection is actually saying, “We don’t spend money on solutions.” Rather, this is a variation of “Call me later,” and should be heard as “We may or may not have budget right now, but I’m saying that I don’t have money to spend on the thing you want me to spend it on.” The best way to handle this is with a response along the lines of “That’s not a problem, because I really just want to understand more about your organization’s way of <your problem space here>. If it turns out we’re relevant, there will be time to talk about that later. Based on what I saw about your <signifier of demand>, I am confident that a ten-minute conversation will definitely be worth your time! Can we schedule something for Thursday?”
“Just send me some information.”
This is another version of “I just want to get off the phone, but I’ll throw you a bone by pretending you can send me information and I’ll read it.” The problem with this, of course, is that there is no commitment to actually consume the information you send. It is very likely it will go in the digital round file.
The right way to approach this, as with the “call me in a quarter” objection, is to capitalize on the fact that you’re on the phone right now. Something along the lines of “I’m totally happy to do that. But if I do, I’m going to do a bang-up job, and it’ll take me thirty minutes to put together something very personalized to you. I don’t want to do that if our solution is not relevant. Can I take thirty seconds to explain what we do, and ask some questions to make sure this is a relevant conversation? That way if it’s not, I won’t be in your inbox chasing you and asking about information that wasn’t even helpful.” Again, you’re trading the prospect time right now for the promise of avoiding pestering later—coupled with a guilt component of “Do you really want to waste my time? That’s not nice.” If you’ve already explained what you do and how it’s relevant, you’ve qualified the prospect beyond a shadow of a doubt, and they still say, “Just send me some information,” take the approach of selling the demo. Try something like “Well, I’m happy to do that. But honestly, given that I know this is relevant to you, a scheduled demo will really be a much better way of making sure you’re fully informed. I promise that you’ll learn things that are very relevant to <the thing they do>.” This way, you’re taking the request for “more information” and saying, “No problem! The best way for you to get the information you seek is on a synchronous, concurrent demo.” Pair that with a promise of downside prevention—a promise that the prospect will not only get the information she just stated she wanted, but will also become a more competent professional. Who doesn’t want to become better at their job?
“Oh, we already use <competition>.”
The great thing about this objection is that the speaker is admitting that she has the problem that your solution addresses, and moreover, that she spends money to solve it. Fantastic! She just partially qualified herself. First, congratulate her on being a student of the game and clued in. Then, all you have to do is succinctly demonstrate why it’s worth the time to look at your solution as a substantially better way to solve her problem.
So, for instance, if someone said to a TalentBin rep, “We already use LinkedIn Recruiter for our technical recruiting search and outreach,” the rep might respond with “That’s great! LinkedIn Recruiter has historically been the benchmark for passive technical recruiting. The good news is that TalentBin can help you find ten times the number of candidates in your area, complete with their personal email addresses, and with no limits on email outreach, unlike InMail. Sounds pretty helpful, right? I’d love to get twenty minutes on the calendar to show you how TalentBin is like LinkedIn Recruiter, with rocket boosters attached.”
“Do you have <X, Y, or Z feature>?”
In this situation, the prospect starts to get deep into features and what your product has or doesn’t have. This is actually a really great place to be, if you handle it correctly. It’s not that the prospect is objecting to your solution, per se, it’s just that he’s blocking your ability to get a formal appointment on the calendar. This is kind of like an abortive “hot transfer” as discussed above, where instead of hearing the whole pitch, having his mental model set correctly, and going through proper discovery questions, the prospect is attempting to have “demo by a thousands cuts.”
The best way to handle this is to “assumptively close” on setting the appointment, as he’s partially admitted his interest in and familiarity with the problem and solution. Something like “These are fantastic questions, and show you really know the space inside and out. Typically folks find it more efficient and get a lot more out of putting twenty minutes on the calendar at a set time. Do you have twenty minutes on Thursday or Friday where we could slot that in?”
“How much does it cost?”
The good thing about prospects asking about cost is that they are admitting that they have the problem, understand to some extent how your solution fits in, and are trying to get a sense of whether the cost fits the pain. The problem, though, is that there’s still a huge information asymmetry here: you don’t yet clearly know the magnitude of the prospect’s pain (because you haven’t asked your discovery questions), and the prospect isn’t anywhere close to understanding all the ways in which your solution can help address this pain. So if you immediately jump to pricing—say, $10,000 a year—she has very little information with which to make a judgment about whether the value the solution provides is worth more (ideally far more) than the price. So you can end up in situations where the prospect responds, “Whoa, that’s way too much.” But let’s say you’re HIRABL, and your solution finds contingency recruiting fees worth $30,000 a pop. A customer passing on a solution that could make them $100,000 for just a $10,000 investment would be a tragedy, but you’d be amazed how common this is as a result of cost objections getting in the way.
The best way to avoid this is to not fall into that trap to begin with. Instead, parry the question and drive to a demo with something like “While the solution does have a cost, it’s really contingent on a variety of factors, associated with how much value a given customer would get out of it. Typically people find it most effective to schedule a twenty-minute demo so we can get a better sense of whether the solution is relevant and how helpful it could be to your business. Do you have twenty minutes this Thursday or Friday for that conversation?”
“I can’t make that decision.”
This objection can indicate one of two things, and it’s important to resolve which. That is, is this person actually the relevant point of contact, and trying to dismiss you? Or is she truly not the relevant contact, and you need to find the correct one (and potentially refactor how you’re doing prospecting if you’re calling on the wrong people)? The challenge is that these two things can look the same if you don’t ask the right questions.
The way to sort this out is to assume that the account does have the pain you’re solving, but that this person could indeed be the wrong point of contact. Drive to sorting out who you should be talking to with something like “Got it! Well, it sounds like this is relevant to <company name>, but that you might be the wrong person to talk to about it. I tried to use LinkedIn to figure out who would be the most relevant contact, but I guess I got it wrong. Which of your colleagues should I be engaging instead?”
You can potentially refer to the person’s supposed manager—for instance, if you’re Immediately, the sales-first mobile email and CRM client, and you’re talking to a Director of Sales Operations, you might refer to the VP of Sales, to whom the contact you’re talking to likely reports. Or potentially the CFO. Or shoot, maybe even the CEO. This tactic helps indicate where you’re going to go next if they don’t tell you, so they might as well be straight. If that person is indeed the right point of contact, and you sound like you’re going to show up on the CEO’s doorstep saying, “Jeff said that he’s not the right one to discuss this, so I’m here to talk to you,” that’s probably not going to look great for Jeff. So he might as well own up that he’s the right point of contact. And now you’re in the same situation as the “I don’t have budget” objection, where it’s less an issue of “not possible” and more a question of “is the timing right?”
If it’s the second case, and you’re actually targeting the wrong person, the contact you’re talking to doesn’t have much reason to obscure who the relevant contact would be. And, again, by indicating who you’ll be targeting next, you create a poor best alternative to him giving you the correct name—that is, if you show up on the CEO’s or CFO’s or VP of Sales’s doorstep indicating that Jeff sent you, and she’s not the right person, well, the CEO, CFO, or VP of Sales will probably not be too stoked. So better for Jeff to just be straight with you and point you in the right direction. At this point, Jeff is acting like a gatekeeper, and you should simply employ the tactics described above to help him understand how beneficial passing you along to the right point of contact will be. Make Jeff look like a hero for bringing your solution to the fore!
Setting up the Appointment
Meeting Invites
Once you have an appointment time and contact information, you need to send the relevant details for the meeting. For very early-stage customer conversations (like your first dozen customers), I’m a fan of going to visit the individual in person. As discussed in the Prospecting chapter, this is why initially targeting accounts in your own geography is helpful, even if the price point of your solution means that your scaled go-to-market will likely be via inside sales. If an in-person meeting is not tenable, you’ll need a means of digital presentation. Zoom and join.me are good for this, as we’ll discuss more later.
Whether the meeting will be digital or in person, all of the relevant coordinates need to be included in the meeting invite you send to the prospect. You absolutely must send a calendar meeting invite. You cannot rely on the prospect to put the relevant details on his calendar, and this is a convenient way to both put the meeting on his calendar and deliver the pertinent meeting details. Put the location details (whether online or offline) in the location section of the meeting invite, in addition to the description section (yes, repeat them)—something like “Online meeting via join.me. Click this link to join: http://www.join.me/yourusername.” Be sure to put a brief agenda in the description section, after the duplicate location coordinates. Lastly, make sure to include a rich title description that reminds both the prospect and you of the goal of the meeting, like “Twitter & TalentBin Online Demo” or “HIRABL & Robert Half In-Person Demo.”
Consider including “teaser” material, like a demo video hyperlink, in the body of the meeting invite. This will help prospects get excited about attending, but shouldn't give them enough information that they feel it can stand in for the actual demo.
Finally, make sure to invite all the relevant participants who were surfaced in your call.
This is a good example:
Time Blocking
After sending the relevant meeting invite to the prospect, make sure to block fifteen to thirty minutes on your own calendar both immediately before and after the appointment to ensure you have proper time to prepare and to follow up. If you don’t, there’s a risk that those slots may get calendared over, and you’ll find yourself double-booked when you should be executing activities in support of your meeting. We’ll discuss preparation activities in more depth later, but you want to make sure that you have the time to treat every appointment with the seriousness it deserves. You would be amazed by the lack of preparation some reps exhibit in approaching meetings that not only represent tens to hundreds of thousands of dollars of potential revenue but, moreover, are the culmination of hours of appointment-setting activities. At TalentBin, we used to call demos “five-thousand-dollar bills,” because with our average contract value and win rate, each demo represented $5,000. This joking terminology helped focus the appropriate amount of attention on the importance of preparation, execution, and follow-up. Lastly, if you’re going to be traveling to the meeting, make sure you block appropriate travel time so you get there with plenty of time to spare.
Remindering
Part of appointment setting is making sure that people actually show up to the meeting. This is more of an issue with digital meetings, because the individual needs to “come” to your join.me or Zoom link. And while attendance is somewhat helped by traveling to the prospect, the worst-case scenario can still happen if the prospect is double-booked. You wasted travel time and weren’t able to complete the appointment. The solution to both of these outcomes is to sufficiently remind the prospect with a good amount of time. You can do this in the meeting invite by setting reminders; I like fifteen minutes ahead of the meeting. Setting one further out than that can be dangerous, because calendar-sent reminders are typically read by prospects as “This is happening right now”; if you set a reminder too early, or set multiple reminders, you can end up with prospects showing up multiple hours early. And unhappy about it. So using calendar-based notifications as anything other than immediate reminders can be a crapshoot. A better approach is email-based reminders. Use something like Yesware or Boomerang’s “Send Later” functionality to stage a reminder email to send early in the morning of the meeting in question. You just have to make sure that if the meeting ends up being moved, you go into your “Scheduled Emails” and modify the date for the staged email.
Aside from ensuring that prospects show up, reminder emails are also another opportunity to set expectations, especially for a first call. Something like, "Hey, Sarah. Looking forward to speaking with you and going over TalentBin. I understand that when we reached out to you to schedule this call, you had expressed specific interest in learning more about boosting candidate response rates and managing existing candidates. I will cover these in depth with you.” This not only provides guidance on what’s going to be covered (so the prospect doesn’t go rogue on you), but also is an opportunity to tease the content.
Cadencing: Putting it all Together
It’s a rare situation where your first email or first call results in a prospect getting back to you and agreeing to an appointment. Instead, you’ll need to implement a series of outreach actions targeting your prospects, typically alternating between emails, calls, and voice mails. In sales, this interleaving of outreach actions over time is known as a “cadence.”
You can of course implement this yourself via your lightweight Google Sheet CRM, or in a more formal fashion through an actual CRM. Or, if you want to get really crazy, there is a set of solutions that are designed specifically to orchestrate this outreach cadence—two primary players being Outreach and SalesLoft. Both have pricing that accommodates an individual inexpensively and can help you be much more efficient in your appointment-setting workflow.
Regardless of whether you’re doing it yourself or using an orchestration system, typically you want to alternate emailing and calling. For instance, that might be an initial email and call on day one, followed by a call on day two, and then maybe a call and a voice mail on day three. From there, you might skip a day, and then email on day five, followed by an “I’m breaking up with you” email on day seven. By no means is this a cut-and-dried approach—you could decide to do calls with follow-up emails every other day, or some other permutation, if it works for you. To some extent, this will be related to how much content you have to share. If you have a lot of great things to say about your solution, and you have lots of video snippets you can add to consecutive emails, your cadence could potentially be longer and perhaps more frequent.
In addition to pure time-based cadencing, you can involve contextual data into this process as well. That is, part of your cadence could be reviewing the previous day’s opens and clicks and prioritizing those prospects for calls. Or it could mean breaking out of your cadence to immediately call a prospect who opened an email when you see the alert. Or it could mean sending an immediate follow-up email to a prospect who just opened one of your emails. All of this contextual activity can raise connect rates and appointment-close rates by focusing on prospects who are already thinking about your solution.
Whatever strategy you employ, it is important to realize that multiple touch points, and a system that requires you to work through them, are core to being successful here. Having a cadence compels you to do the actual wood chopping to connect to your prospects, where you will have a chance to book them for an appointment.
Referral Prospecting
With the advent of social networks like LinkedIn and Facebook, it has become far easier to understand who someone knows, and thus, could potentially refer you to, than ever before. This can be helpful for prospecting, and reduce friction for getting your foot in the door to set an appointment.
Doing this at small scale can be a great way to initially supercharge your pipeline, but it will eventually run out of steam, in that you, your team, your investors, and so on will eventually run dry. So while it can’t be a long term solution necessarily, it can help early on.
Connection Discovery
First, note that referral prospecting is not about selling to anyone who will take a meeting because they know someone in your organization. Rather, it is about using relationships within your organization to more easily access accounts that you know are qualified and have the pain your solution solves. So just be clear on which direction the causality runs here.
That said, there are two ways you do this. One is with contact connections and the other is with account connections. In the first case, you look at the target
How to do this? We’ll discuss a more manual process first, before talking about ways to do this in a more automated, scalable way. First, LinkedIn and Facebook connect with everyone in your organization, your investors, and your advisors. This will make it such that when you look at a prospect’s LinkedIn or Facebook profile, you’ll be able to see if any of your organization’s stakeholders are shared connections.
Once this is done, visit the LinkedIn profile of decision maker prospects you identified in your prospecting exercises. If you want to just test this out, start with 100 decision makers, like Directors of Talent or VPs of Sales or CFOs or whatever the decision-maker is for your solution, and see which of your organization’s stakeholders are joint connections. Note which of those stakeholders are potential referrers, as we’ll be using it later.
Once you’ve done this, reach out to each of those joint connection via email, ask them if they would be open to connecting you with the target in question, specifically noting who I want to get in contact with, why it will be valuable to that target (that is, not a waste of their time), and lastly noting to the potential referrer that if they’re willing to connect you, you’ll send an introduction request email with full context to forward along. If a given shared connection is indicated for more than one target contact, aggregate all the targets together to note to them all at once who you’d like their help engaging with.
The other, more exhaustive, way you can do this is to sit together with each of these stakeholders, and together manually go through their LinkedIn networks. This can take an hour or two, but will invariably be worth it. This approach is particularly helpful in that you can be more thorough than the approach above—however it requires a stakeholder to sit with you, so can be more friction, but it can be worth it—and while you’re going through their connections you can look for titles that are attractive, even if it’s not a “VP of Talent”, which would be your ideal contact, if instead they know a “Recruiter” or “Recruiting Manager” at the target company, that can be better than nothing, and, failing that, you can look for senior staff who work at a target company, even if they’re not in the right part of the org.
That is, to use our recruiting example again, even if a staffer or advisor isn’t connected to a single “VP of Talent” or “Director of Recruiting”, he might be connected to a peer of that contact in the target organization. So look for titles like “VP” or “Director” at organizations that would be qualified. As you’re going through contacts together, you may be able to quite easily identify some of these target organizations by name, but even if you can’t, just log the LinkedIn profile of the relevant contact, and you can go back and qualify their organization after the fact. The goal of this session with your colleague is to quickly identify relevant contacts that they would be willing to introduce you to—you can do other legwork later.
When I say log these profiles as you’re going, it doesn’t have to be complicated. Just stand up a Google Spreadsheet and while you sit with your referrer, just copy and paste the LinkedIn URLs into cells for you to later prioritize and go through—typically it can be easier just have them log into LinkedIn on your laptop and you can drive, and all they have to say is “Yeah, that person’s great” or “No, I don’t know her well.”
Contact Outreach
After this session is done, go back through the relevant contacts, and qualify their orgs to ensure that they’d be a fit for your solution. Again, we don’t want to be introduced to organizations that don’t have the pain we solve—it will be a waste of our time, and theirs. Once we have that list, you’re going to send the referring stakeholder an introduction request email for each of the target contacts. That is, we’re going to make it as easy as possible for them to just forward something along with their compliments. We’re not going to rely on them to act or come up with messaging, or anything like that. We want this to be as low friction as possible.
This email should include a subject like “Intro to <target contact’s name>?” and within the email should detail why you want to get introduced to them, and how it will be valuable to them. Specifically, you should characterize why you know their organization is qualified for your solution, and a terse statement of the clear value it would provide and the problems it would solve for their organization. So not dissimilar to the outreach emails above where we characterize the research we’ve done. But in this case, we’re making it easy for our referrer to just hit “forward” and pass the outreach along, or just CC you into the thread, along with their comments as to why you’re a worthwhile and trustworthy person to connect with. That is, our goal is simply to use our referrer as a reputation provider—they are validating that we are legit, and approving the statements we make in our introduction request email.
When you send the introduction request along, use something like Yesware or other email tracking services to put a tracking pixel into the email. This way you can see if indeed the email was forwarded along, by seeing how many unique IP addresses opened the email.
If your referrer CC’s you into the email thread, be ready to quickly put them to BCC, and send a thoughtful quick request for a call, ideally providing a set of times and dates a week out or so, or, if the target is a peer of your ultimate target—i.e., this is a case where the target is the Director of Customer success, and you want a referral into the Head of Recruiting— quickly note that, and who that ultimate target person is (you should have sniffed that out ahead of time, and potentially could have noted that in your intro request). But speed is of the essence, in that you want to look like you’re on top of things.
If you don’t hear back from the target of your intro request, all is not lost. I typically recommend that you go directly at the target contact, using the same email thread, and take another shot at convincing them you’re worth take a call with. Use the same email thread because it will have the reputation value of your referrer being willing to introduce you. But after that point, good to move on to another contact.
Typically it’s a nice touch to hook up your referrer with a gift card for taking the time to go through all of her contacts with you. And then if you end up closing a deal based on her referral, well, maybe add another gift card on top of the original!
The above is a more manual way of going about this, but if you want to get more scalable, you can use software like Teamable to consolidate all the contacts of your staff, advisor, investors, and so forth into a unified database that you can query for titles and company names, and will reduce friction in the email outreach part of this process. Given that these referral deals can move very quickly if properly executed, the return on investment on dedicated software to facilitate it can be very compelling.
Inbound Lead Capture and Response Preview
The last thing I want to cover on appointment setting is the basics of inbound lead capture and response. We’ll get into this in more depth in the following chapter, but want to touch on a number of key points, briefly.
As a result of your outbound appointment-setting activity, invariably you will generate what is known as “inbound” interest. That is, people will read your emails and click on the links to your website to learn more. They’ll listen to your voice mail, open Google, and search for your solution. And if your website, along with your primary outreach materials, does a good job convincing them it’s worth engaging, you’ll want to make sure that you can take advantage of that and easily allow them to become “inbound leads.”
The basic requirement for capturing these leads is a means by which someone on your website can get in touch to express interest and engage with you. We’ll talk more about lead capture forms in the next chapter, but to start this can be as simple as a big button that says “Request a demo,” with a mailto: hyperlink to send an email to <sales@yourcompany.com>. If you want to get more involved, maybe even utilize the “subject” and “content” tags to pre-fill some information like “Demo Request for <Product Name>,” so the prospect doesn’t have to write anything. The more advanced version can be a Google Form linked from that button. Seriously, this doesn’t need to be rocket surgery to start. You want prospects to be on that page, say, “Huh, yeah, this does sound good. I would like to learn more. <Click>,” and be on their way.
The next step is making sure you know someone’s trying to get in touch with you. An easy version of this is an email notification that is generated from whatever form or mailto setup you choose. The notifications should show up somewhere you know you’ll be able to check on a fairly frequent basis. I like email notifications that are automatically foldered, such that when I pop into my email, I can see if that folder has gone bold with a little unread number count next to it.
Lastly, the most important thing about inbound leads is that you need to respond to them fast. We’ll talk about qualification of inbound leads later, but even ahead of that, it’s critical to respond to inbound leads as quickly as they come in. Don’t let them wait around—they’re excited now. At a minimum, you need to start the conversation immediately. Otherwise you’re not capitalizing on all that hard work you did garnering their interest. Grab ahold of it, and set the appointment!
In summary, business-to-business sales are very rarely a “one-call close” situation. Regardless of what you may have seen in Boiler Room. Rather, it's a stepwise process that starts with identification, and then progresses to selling the prospect on a more formal evaluation. Appointment setting is the way to make that happen. Use thoughtful, methodical outreach strategies, and you will be putting appointments on your own calendar like a machine, teeing yourself to slam them shut come demo time.
Further Reading:
More on outbound appointment setting in Leading Sales Development, The Sales Development Playbook, Fanatical Prospecting, Predictable Prospecting, and Sales Development.
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