Founder-Led Prospecting, Ep. 3
Our previous installment ended with us gaining an understanding for the contrast between personalized approaches and those that are automated. But we hadn’t yet discussed how to actually compose outbound copy. And we had teased that exercise started with conjuring up our ingredients. Our outbound copy building blocks. So let’s dive in.
Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your third installment.
For any given vertical you’re going to be targeting, you’re going to want to come up with building blocks for your outbound copy. That starts with deciding who you’re targeting with your outbound motion. You could say, “I’m going after CTO’s at Series B startups.” Or, “We’d like to sell to recruiters at Fortune 500 companies.” Once you decide on an initial vertical you’re aiming at, you’re going to want to come up with at least 10 options in each of the 5 outbound building blocks categories. Why that many? Well, you want to give yourself plenty of ingredients from which to choose to come up with many outbound copy variations. Remember: it’s almost impossible to know what message will resonate until it’s tested in market. We might have opinions or guesses, but until we’ve tried it on prospects, we just don’t know. Giving yourself plenty of building blocks will give you plenty of at bats. (By the way, we’ve developed an outbound copy building blocks worksheet we run our clients through. If you’re interested in getting a copy of it, just drop me an email at paul@gassee.com. Or better yet, reach out and I’ll guide you through it myself in a complimentary coaching session.)
Let’s talk about pain points first. They are by far the most important of all building blocks. “Now, why is that?”, you might ask. Well, there’s an old (not that old, as outbound hasn’t been around for centuries) saying in outbound. That goes something like this, “You get a lot more from leading with pain than you do leading with gain.” And it makes sense, if you think about it. When you lead with something difficult your prospect deals with, you’re showing your prospect you understand them. You are wrapping your arm around them. Empathizing with their day-to-day. This ends up earning you the right to pitch. Versus leading with what makes your product special. That generally turns off your prospect, as it feels to them like you’re trying to shove your product down their throat. As a matter of fact, we’ve written potent copy with our clients that is pretty much just a pain point, and not much else. It’s powerful because you’re able to hit a nerve in your prospect. They feel seen. They open up. And end up leaning in and wanting to engage with you. “If this guy is telling me the truth about being able to solve my hair-on-fire problem, I need to chat with him” is likely a version of what they’re thinking. Next thing you know, you’ve got an interested reply in your inbox. When we’re prompting our clients to come up with pain points, we’ll tell them, “Put yourself in the shoes of your prospect. You’re laying awake at night tossing and turning. What pain in your work life can your product eradicate? If you need to use ‘I’ statements to really inhabit your prospect’s world, feel free to do so.” Good examples of a pain point? “I’m wasting a ton of time on manual tasks.” Or “I’m afraid I won’t be able to deliver our product on time because my technical team is too small.” Or even, “I’m struggling to hire good salespeople and it’s making it hard for me to hit our revenue target.”

Next up: value props. Those are high level benefits your product or service provides your customer. Not a feature or functionality – which is where founders will go a lot of times. People don’t care about those. Or about acquiring a new piece of software. Folks buy outcomes. Pain eradication. Emotions. Feelings. And you have to realize that our inboxes all get invaded with commercial offerings. Thus the importance of having your value props be differentiated. You want to be able to stick your neck out and plainly state “This is how we’re different.” You want your prospect to read your message and think to themselves, ‘I haven’t heard of a product that does this. Wow…feels like a novel approach.’ Example of a good value prop? “Our product is the only one in the market that gives you peace of mind while reducing your workload.” Or, “Customers have reported that our platform has reduced their sourcing time by 66%, more than any other product they’ve tried.”
Quantifiables is our next ingredient. They are all about answering this question, “What is the size of the impact of our solution?” You want to get folks leaning in because they realize how much you can affect their lives. If you tell prospects they’ll get 15mins back per week by using your product, all while asking them for a 10-min intro call, folks might think you have a cool offering. But in the end, they’ll most likely think they can skip having an intro call. 15mins back per week for a 10mins investment just doesn’t move the needle. But, if you told them they get 15 hours back from using your product? That’s almost two full work days. Prospects quickly grok they could be doing a lot with this new time afforded them. Like, spending more time with family. Or working on the golf game they’ve been ignoring for years. One thing we tend to forget too is that human beings process numbers differently. For the example of, “Our customers get 10 hours back per week on average.” You could also express this quantity as: 25% of your week back. Some prospects will feel like 10 hours is more tangible. Others will see 25% as a larger chunk of time. The amount is the same. But folks have different ways of taking in numbers. Relating to them. And what we need to do as go-to-market practitioners is to test both out and see how our prospects react.
What have others said or done that increase our perceived value to customers? That’s social proof. And it’s our next building block. Those can include customer logos, testimonials, case studies, of course. But also things like high-profile investors in our startup. Or press mentions. Or even prominent companies that are in the founding team’s background. “Having just launched 3 months ago, Uber and Google are already customers of ours” might be social proof you’d included in an outbound LinkedIn message. My reaction receiving this as a prospect would be to think, ‘Whoa. These guys have only been in market for three months and already have those logos. They must be on to something big! They’ve got my attention, now…” Next in my mind would be, ‘What are these guys doing that is so good? Perhaps I need to just take a call with them to find out more.’ As you’re already noticing, social proof is your calling card. It’s having other entities than yours telling or signaling to the market that you’re special. Worth paying attention to. And it’s very powerful. So, when putting it together, get in your prospect’s skin. What would impress them most? What would have them quickly go from discarding your email to saying to themselves, ‘Man, this company is working on something worthwhile.’ Remember, as an early stage startup, we don’t have the benefit of an established brand or of marketing air cover. If you get an email from a rep at Salesforce, you’ve got a story about them. Perhaps it’s ‘most successful CRM of all-time, Salesforce tower in San Francisco, Marc Benioff.’ If you received a LinkedIn message from a salesperson at Apple, you might think, ‘Steve Jobs, the iPhone, Tim Cook.’ You have a narrative about the tech giant there too. As nascent startups, we’re mostly an unknown quantity. Putting yourself on the map with great social proof changes the way you’re perceived.

For our last ingredient? The call-to-action/offer. A critical component that generally doesn’t get enough attention from founders. Despite the fact that it has shown to be the difference from a lackluster outbound campaign to one that takes off. Generally, founders will have a “quick 15min call” or a “product demo” as their CTA/Offers. And those should be tested. But you have to realize that a lot of prospects receiving an outbound message from you will still be sitting on a razor’s edge about taking an introductory call with you. Before your message, they most likely hadn’t heard about your company or product. You might have sent a crisply worded 5-8 sentence message. But there’s a great likelihood your recipient is thinking, ‘Boy, this product sounds cool. And I could probably use it. But, man am I busy right now. Not sure we could even implement it.’ That’s where you need to deliver even more immediate value to your prospect. What above and beyond your product can you offer your prospect in the 15-min call they’d be taking with you? What can you dangle that would have them say a sure fire “yes!” to joining you on a Zoom? The answer to that question unlocks a whole lot of interested replies. Follow me down this fictitious rabbit hole for a second. Let’s imagine that instead of selling your current product, you’re peddling a SaaS tool for sales coaches. I know I know…I did ask you to come with me to this made up place. But let’s imagine you composed the following message:
Hey Paul,
Are you struggling with menial tasks?
If so, we should talk. We’ve spent the last two years building a product that should completely eliminate those. The average sales coach using us gets 15 hours back per week.
Have 15mins for Zoom in the coming week to see if there’s a fit?
During that call, we’re more than happy to share the top pitfalls sales coaches fall into that prevent them from making their highest possible income. These have been amassed over the 200+ conversations we’ve had with sales coaches like you over the past two years.
Cheers,
[Founder]
Now, I consider myself a top sales coach. But I’m not arrogant to think that I might not learn about one or two pitfalls I’m falling prey to. And that just by bringing those into my awareness could have a 5 or 6 figure impact on my business. All of a sudden, I go from reading this email and thinking, ‘Wow, this is a cool tool…I could potentially use it. And if they’re quantified impact is true, I might be able to do a ton with this gained time.’ To, ‘The tool sounds great. But I need to take this call. Regardless of whether or not I can use it, I could learn something super useful from this founder, that could have a significant impact on my business.’ I’m no longer straddling the fence, but taking the intro call ASAP.
You’ve got your ingredients for outbound copywriting. And they’re beautifully prepped. The “mise en place”, as chefs call it. Now how do we create a tasty meal from those building blocks? That’s where we’ll start next week. I’ll do my best to deliver best practices in outbound copywriting. See you then.