prospecting for interviews

Good morning Predictable Revenue community,

Reminder to all that signed up for my Advanced Reader Copy (ARC) program, I’d like to include some of your reviews / comments in the actual book. If you want the chance of being in there, I need your replies in by March 5th. If they come in after, they’re still helpful but they’ll be on the website or Amazon page.

I’ve had a few of the same conversations this week and that’s usually a good sign it’s top of mind for many of you so today we’re talking prospecting for customer development interviews. 

tl;dr - if you’re under $1m in revenue, you probably should be reaching out and asking for advice instead of running traditional sales outreach. 

One of the biggest struggles I see founders wrestle with is moving to sales mode. Especially when it comes to finding people to sell to. I’ve written about this before when it comes to selling to folks that participated in customer development interviews. But what about when that well runs dry? Many founders get stressed because they don’t know what to do next. But the obvious channel is staring right at you, more customer development interviews.

I get a lot of resistance to this idea because founder feel like they’re going backwards. I get it, doing more customer development interviews feels slow to start. But, as I’ll show you with real life math, it’s a more efficient method for reaching prospects AND has the added benefit of helping you learn along the way. 

When you jump into prospecting as soon as the product is “ready to sell,” you likely won’t know enough to really dial in a sales development campaign. This is, in part, because your product and who it serves are still likely to shift a little. If you move forward with prospecting, you’ll likely have a bunch of unvalidated assumptions baked into your approach—who you’re reaching out to, what specific pain they have, how your solution fits, even what channel they’re most active on. All it takes is one wrong assumption, and the whole thing collapses. It’s like a chain link system: if any single link breaks, the entire chain is compromised. 

In contrast, when you’re asking for advice, you open the conversation in a much more collaborative way. People are happy to help someone who’s curious and eager to learn—it’s more appealing than being sold to. It doesn’t matter if your targeting is off because in the worst case scenario, you get the opportunity to learn from someone outside of what you thought your core profile was. And don’t worry: you can always sell to them later, once you know they really do have the problem you can solve and want to fix it. 

Here’s how to think about it: instead of firing off cold sales emails, we use these same tactics to book customer development interviews. When you switch from “Can I sell you something?” to “Can I learn from you?” your reply rate can easily 5x. (Mine jumped from below 1% to 5% on my latest campaign.)

Why the jump? Because you’re not leading with a sales pitch—you’re leading with genuine curiosity and a willingness to adapt. This tactic only makes sense if you’re still open to changing your product or approach based on what you learn. Once you have a mature roadmap, a full product, and more than $1M in revenue, it’s harder to play the “small startup” card. You can—and should—still ask for feedback, but this particular tactic won’t feel as authentic.

Let’s look at a typical outbound sales process:

• Cold sales email nets about a 1% reply rate and 30% convert to a meeting. So if you send 1k emails, you’ll book 3 meetings per week.

• Assume that 30% of those meetings become opportunities and you’ll close 20% of them (which might be generous for outbound). 

• That means you need about 5 weeks of prospecting just to land 5 real opportunities and (hopefully) 1 sale. 

• Then add a 2-week sales cycle, and you’re looking at 7 weeks to get that first win. And that’s only if you already have the machine running smoothly—getting it all set up can take 2–3 more months.

• In the process, you blasted 5,000 total contacts—so your sales efficiency is 1/5,000 (0.0002).

Now let’s look at a customer development approach:

• Let’s assume a customer development email nets around a 5% reply rate with 80% converting to a meeting. These are the stats from a customer development campaign I’m running for myself. 

• That means 1k contacts should result in 40 interviews. 

• Let’s say you spread those 40 interviews out over a month (about 10 per week). If you’ve identified a real, painful problem, 10% of those interviews should convert into paying customers. 

• That means in about 10 weeks, you get 40 interviews and 4 future customers.

• Even though this adds 5 more weeks to your overall cycle, you’ve contacted 1k people, learned from 40 different prospects, and closed 4 deals. That’s a sales efficiency of 4/1,000 (0.004).

The customer development approach (0.004) is 20x more efficient than the standard sales dev approach (0.0002). And you end up with invaluable insights that shape your product and messaging going forward. That’s going slow to go fast.

As for channels, I’ve tested this over LinkedIn and email. Both work as long as your target audience is active on the platform, and most people are active on email. 

On LinkedIn, you can add 30 people a day, wait for them to accept, and then message them. Usually 20–30% accept (depending on industry), so that’s 9 new connections a day. If your targeting is good, 5–10% of those people might book a meeting—or 1% if your audience doesn’t use LinkedIn or you’re off the mark. Booking 5 meetings a week is excellent, 2–3 is okay, and 1 every two weeks probably means you need to recheck your approach.

Finally, let me just say: cold outbound isn’t evil. You can definitely beat the standard metrics if you do it well. Just remember, targeting is the most important element of any campaign. If you’re contacting a wide, generic audience, expect average (or worse) results. If you’re laser-focused on a tight group that cares deeply about a specific problem, you’ll see much better outcomes.

On the AI SDR front, I have mixed feelings. My biggest complaint is that AI tools often abstract away the most crucial step—building high-quality lists and creative campaigns. The plus side is you can personalize at scale, which can help deliverability if you do it correctly. But if you rely on AI messaging to paper over a mediocre list, it’s not going to help you much. List quality trumps fancy messaging every time. That’s why I’m intrigued by Apollo.io’s new AI Messaging feature. It could be a game-changer if it truly lets you combine great targeting with AI-driven messaging. It’s early, so we’ll see. But I really like the idea of having more control over my campaigns and still getting the benefit of AI messaging. 

Bottom line: if you’re under $1M ARR, back off the hard sell and focus on customer development. Yes, it might be a little slower in the beginning, but you’ll build a better foundation, learn more, and set yourself up for faster growth in the long run. Once you cross that $1M mark, you can still ask for feedback, but it becomes trickier to maintain that “We’re just a small startup” vibe. So use this tactic while you still can—and watch how much faster you learn, adapt, and ultimately close deals.

Happy prospecting.

Collin 

PS - yes, I promised to send some invites for the community this week. No, I didn’t have time to do it. I was onboarding two new clients and that took up a bunch of the time I had planned. Keep your eyes out next week… hopefully.

PPS - the pre-order page is officially up on Amazon and I’m pumped. I’ll definitely have some bonuses for those who pre-order, if you have any ideas, hit me back here.