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Updated August 22, 2022You’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.
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. 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.
Given the activity-centric nature of sales, you’re going to have many balls in the air concurrently. As noted in Mindset Changes for First-Time Sales Professionals, 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 Early Prospecting. 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.
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 (for example, number of recruiters, number of open jobs, site traffic, and so on), a set of outreach emails with supporting collateral (such as 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 unskilled 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 voicemail/email if you will. Who doesn’t like it when someone makes them a personalized love letter?
cautionEmail 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.