Connor Nelson's Unfair Advantage in Enterprise Sales (And Why Your Sales Team Is Basically Playing Chess While Blindfolded)

The verdict is in: most enterprise sales reps are out here treating human beings like walking procurement departments with LinkedIn profiles.

And then they wonder why they're losing deals to competitors with inferior products.

Chef's kiss. Beautiful self-sabotage.

The Weekend That Changed Everything

So I'm talking to Connor Nelson on the podcast this week—guy's an enterprise AE who's built his entire book of business on not being a robot—and he drops this story that honestly made me feel feelings.

Picture this: He's on a Monday call with a prospect in Minnesota. Asks how the weekend was. Dude mentions he couldn't do a planned event with his son because—Minnesota weather, naturally.

Here's where it gets spicy.

Connor doesn't just nod and move to the discovery questions like a good little sales bot. No. This madman goes and researches family-friendly events in the area for the NEXT weekend. Sends the prospect a flier with: "Hey, want you rested and recharged for our next meeting."

The prospect shows up to the next call basically treating Connor like a friend instead of a vendor.

Meanwhile, your sales team is sending generic "circling back" emails and wondering why their close rates look like my portfolio in 2022.

The RBE That Nobody's Teaching

Connor introduced me to this concept from his RingCentral days: RBE (Relationship Building Exercise/Experience). The idea is stupidly simple—with every single prospect, you need at least ONE genuine human connection moment early on.

Not "Hey, I see you went to State U, Go Wildcats!"

I'm talking about actually noticing something in their Zoom background. The books on their shelf. The Marvel shirt. The anything that shows they're a human with interests beyond your Q4 numbers.

Then—and here's the part that separates the adults from the children—you actually do something with that information. You research. You send a relevant article. You ask a follow-up question two calls later that proves you were listening.

It's almost like... treating prospects as humans leads to them treating you like a human instead of an interruption to their day? Wild.

Why Your 9-Month Sales Cycle Is Actually Your Superpower

Here's what Connor said that honestly broke my brain a little:

In enterprise sales, you're looking at 3-12 month cycles. That's 20-30+ calls before implementation. Most sales reps see this as a grind.

Connor sees it as 20-30+ opportunities to build an actual relationship.

Because here's the thing nobody tells you: your champion in that deal? Their career is literally on the line. They're going into rooms with VPs and C-suite folks, vouching for your six-figure solution. If it fails, they're cooked.

You think they're picking the vendor with the best feature list?

Hell no.

They're picking the person they trust. The person they actually like. The person who sent them that event flier for their kid.

People buy from people they like. Full stop. No cap. Every other strategy is just expensive theater.

The Instant Gratification Trap (Or: Why You're Burnt Out)

Connor dropped this truth bomb that honestly should be required reading for every sales leader:

"If you can't remove instant gratification from your mindset and just enjoy talking to another human being, you're going to burn out hard."

Think about it. When you're obsessed with the commission check at the end, every call is just another slog. Another procurement meeting. Another technical deep-dive.

But when you're genuinely curious about the person? When you're present in the moment? When you realize this is actually an opportunity to make a real connection?

The job becomes... fun.

Revolutionary concept, I know.

And here's the kicker: even if the deal falls through, that person you built a relationship with? They're moving companies. They're getting promoted. They're recommending you to their network.

You're not just playing the short game. You're building a career moat.

The Tactical Shaet That Actually Works

Okay, enough philosophy. Here's what Connor does that you can steal today:

1. Camera. Always. On.

No exceptions. Bad hair day? Don't care. Didn't sleep well? Still on. You're the face of your company to that prospect. They need to see you're a real human who gives a damn.

Bonus: When your camera's on, they feel pressure to turn theirs on. Now you can see their Marvel shirt or their bookshelf or their rescue dog in the background. Notes. Taken.

2. Show Up Early

Not to seem professional (though that too). But to have the small talk. That's where the gold is. Ask open-ended questions:

• "How was your weekend? What'd you get into?"

• "How's your week going? Anything fun happen?"

• "Any exciting plans coming up?"

Then—revolutionary concept—actually listen and remember what they say.

3. Curiosity Without Agenda

This is the hardest part. You can't be curious while mentally calculating your commission. You have to genuinely give a shaet about them as a human first, prospect second.

If you can't do that? Enterprise sales isn't your game. Go sell commodities where relationships don't matter.

The Part Where I Get Real With You

Look, I started this podcast because I kept seeing companies obsess over tech stacks and growth hacking and "disruptive innovation" while completely forgetting that business is still human to human.

B2B? B2C? Cute labels. It's all H2H (human to human) at the end of the day.

Your clients? Humans.
Your employees? Humans.
Your stakeholders? Also humans.
(Shocking, I know.)

And humans do business with humans they like and trust.

Connor's out here proving it every single day in enterprise deals where products are basically commoditized. He's winning not because his solution is 10x better. He's winning because people actually want to work with him.

That's the game. That's always been the game.

The Bottom Line (For the Skimmers)

In today's uncertain, disruptive market where everyone's trying to do more with less, your competitive advantage isn't your feature set. It's not your pricing model. It's not your fancy AI integration.

It's whether your prospects feel seen, heard, and valued as human beings.

Connor's building authentic client connections in an industry where most reps are still sending spray-and-pray cold emails and wondering why their pipeline's dry.

Be like Connor. Or keep losing deals to people who are.

Your call.

P.S. If you're reading this thinking "this sounds exhausting" or "I don't have time for this relationship stuff," I have bad news: you're exactly the person who needs to listen to this episode. Your burnout isn't from working too hard. It's from working without purpose. Give a shaet about people and watch what happens to your close rates. Also, Connor mentions he literally lost deals to inferior products because the other rep had a better relationship. So yeah, keep skipping the relationship building if you enjoy explaining to your VP why you're at 60% of quota.

[Watch to the full episode here] — Trust me, it's 19 minutes that'll make you rethink your entire sales motion. Or at least make you stop sending those "just checking in" emails that everyone deletes.

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.