Sales Leaders Are Doing It All Wrong with Ajay Singh

You think you’re ready to scale. You’re not.

You’ve had a few good calls. Maybe a pilot. Perhaps even a close. But if you’re still guessing who your real buyer is, what their urgent pain is, or what message actually lands, you’re not scaling. You’re still searching.

In this episode of The Predictable Revenue Podcast, Ajay Singh, founder of Pepsales, joins Collin to break down how his team ran 200+ discovery calls before writing a line of code, and why that depth changed everything: their ICP, their positioning, even who they refused to sell to.

But this isn’t just a story about Ajay. It’s a roadmap for any founder trying to earn product-market fit the hard way, by talking to strangers, chasing clarity, and pushing past the false signals that kill most startups.

You Don’t Know Enough Yet

If you’ve only talked to 10 prospects, you’re still guessing. You don’t know the real problem. You don’t know who feels it most. And you definitely don’t know what to build.

The founders who get it right don’t start with tools or roadmaps. 

They start with volume. Not 10 calls. Not 20. Think 100+. Structured, painful, repetitive conversations until the patterns are impossible to ignore.

That’s how you figure out:

• Who actually has urgency, and who just wants to “learn more.”
• Where internal workflows are breaking down (not just what people say is broken).
• Which customer segments will burn your time vs. move fast and teach you?

Ajay Singh’s team ran 200 of those calls. That’s how they found their wedge and avoided building for the wrong buyer. You don’t need 200. But if you haven’t heard the same pain 10 different ways from 50 real users, you’re not ready to build. You’re still validating a fantasy.

Most Deals Die in the First 10 Minutes

You’re probably overthinking the close. Discount strategy, objection handling, fancy decks. None of it matters if the first 10 minutes of your call are weak.

That’s where deals die. Not later. Not after the demo. Right up front, when the buyer realizes you don’t actually get their problem.

The best teams don’t win because they’re slick. 

They win because their discovery is sharper. They ask the questions others don’t. They surface urgency. They spot real pain, fast.

This is the part of the call where most founders improvise. They riff. They explain. They hope the buyer connects the dots.

That’s a mistake.

If you want shorter sales cycles and higher close rates, stop tweaking the pitch. Start fixing the front of the call.

Skip the Friendly Feedback Loop

Your network is lying to you. Not maliciously, but because they already like you. They’ll take the meeting. They’ll say it’s interesting. Some might even say they’d use it.

None of that means you have something that sells.

Founders who only chase warm intros stay stuck in a false signal loop. The only way to know if your positioning works is to put it in front of people who owe you nothing.

Cold outbound isn’t just for pipeline, it’s for learning. 

Does the message land? Does the problem resonate? Do they even open the email?

Selling to strangers forces clarity. It strips away social padding and shows you exactly where your pitch falls apart.

If you can’t get meetings cold, you’re not ready to scale warm.

You Don’t Have PMF If You’re Still Pushing

You shouldn’t have to convince people to care. When you’re close to product-market fit, the energy flips. Buyers lean in. They ask the following question before you’re ready. They chase you.

It doesn’t feel like pitching anymore. It feels like triage. They’re venting. You’re nodding. The call turns into a working session. And when the demo ends, they don’t thank you, they ask what’s next.

You don’t get that energy by refining your pitch. 

You get it by solving something tangible, so real that people need it to work.

One signal you’re not there yet? Every deal feels like a grind. You’re pushing. Chasing. Convincing. That’s not sales, that’s denial.

PMF doesn’t feel like a funnel. It feels like gravity.

Your Product Isn’t the Hero. Their Workflow Is

Most founders overbuild. They chase feature parity, stack complexity, and try to impress with depth. But buyers don’t want more, they want familiar.

If using your product means unlearning how they already work, you’ve added friction. And friction kills deals.

The smartest teams don’t try to reinvent the customer’s workflow. 

They slide into it. That means aligning with how the buyer already qualifies deals (MEDDIC, BANT, etc.), how they run meetings, and how they report up.

You’re not trying to prove how advanced your product is. You’re trying to make it obvious how fast they can win with it.

Customization > complexity. Adaptation > reinvention. Fit wins.

Conclusion

Most teams want to skip to the fun part, scaling. But if you’re still guessing, still pushing, still clinging to friendly intros and long-shot demos, you’re not ready.

Ajay didn’t get lucky. He got obsessed with the boring, difficult, necessary parts, discovery, cold outbound, pattern-matching, and real pain. And it paid off.

This episode is a reminder:
1. Before you build a process, build conviction.
2. Before you hire reps, close real strangers.
3. Before you scale, make sure you’re not scaling a lie.

Listen in, and then go do the work.

And, if you’re a founder looking for help in any step of this process, hit us up! We can help.

NO TIME TO READ?