We have more sales and marketing technology and channels to reach our customers, but they’re increasingly tuning us out.

In short: we’re getting more disconnected from customers.

Something is missing.

Even though our tools have become smarter with AI and machine learning, connecting and building B2B relationships has never been harder.

The question is:

How can we connect better and build relationships with B2B customers?

That’s why I interviewed Steve Woods (@stevewoods), Founder & CTO  at Nudge to learn how we can be connecting and building B2B relationships with trust and empathy,

What inspired you to start-up Nudge?

Sure thing. You and I have known each other, obviously, for a long time. A few decades. So, my history before Nudge was Eloqua, in the marketing space, obviously, it’s a space you’re very familiar with, you’re working a lot with marketers.

And really, we were able to see this wonderful transition as marketing went from kind of an arts and craft discipline to a very measured lead generation, demand generation-oriented discipline that started to connect with sales. Here are leads that are qualified; that are interested.

And, that was a wonderful transition to see. But, looking over the fence at the world of sales, we realized that the core of getting those deals done was the next step.

Building trust and relationships

The core was getting the trust and the relationships (and the breadth and depth of relationships at our organization) that would then allow that deal to be moved forward.

The trust and the empathy to be developed, and ultimately the deal to be closed based on those relationships.

As the Eloqua story was winding down, Paul and I decided to jump in and tackle relationship intelligence and use relationship intelligence to understand where empathy is being built, where trust is being built, and how you can make a sales team more effective, by focusing their efforts on the right initiatives.

Brian: That’s cool, just how you took your story from where you were to what you’re doing right now.

Growth lessons: relationships, trust, and empathy are the core

I think the thing that we were lucky with, more than anything, in Eloqua was being part of a major change in a space. Marketing going from unmeasured to measured, and all the effects that that had on the people and the processes and the technology and the understanding.

We were lucky to be a core part of that, and that helped us kind of flow along with that river.

I think what we were trying to do with Nudge was to be a little bit more proactive and say, “What’s going on at a macro level that is going to be a dominant theme of a space for the next decade?”

And looking at sales and looking at relationships, it became very clear that relationships, trust, empathy were the core thing, and it was unmeasurable.  It was intuitive.

Dealing with deal slippage

Every sales leader, when you’re talking about deal slippage when you’re talking about deal progress, when you’re talking about your forecast, it’s all about the relationships and the trust, but it’s not measurable. It’s self-reported by sales reps that often have kind of “happy ears” on the process.

And so, we thought, “If we can do that, if we can figure out how to put a measurement on trust, empathy, and relationships, and then build the tooling on top of that to help people steer the ship in the right direction, then we’re going to be part of a very interesting transition.”

And that’s turned out to be true, as you see sort of the evolution of the sales space: an interesting place to find ourselves in the middle of.

Brian: Yeah. Before us having our interview, we were talking about some of the changes that have happened in sales, and just what’s been happening for our customer, and how difficult it’s gotten for people to get things done, including buying. And one of the things that got us reconnected is, I read the post you wrote about holding the hustle.

What inspired you to write about holding the sales hustle?

Absolutely. That, as with many things, stemmed from a rant, which is always a good place to start.

And it’s interesting because we’re working in this space of sales, so we spent much time and developed a series called “How I Buy,” that interviews buyers and how they go about buying.

Buyer and Seller Differences

And then on the other side, we spent a lot of time talking with salespeople on how they sell.  It was Mars and Venus.

Buyers are all about developing an understanding and kind of guiding themselves down a journey, selectively bringing in salespeople when they need some deeper points of view, and really wanting them to be thoughtful, co-conspirators on a journey.

Then you talk with salespeople and it was automation, it was numbers, it was a thousand emails a day. It was, “Hey, did you get my last email sequences?”

It was all hustle, hustle, hustle and it was bizarre to look at these and realize that they were attempting to describe the same animal.

It was bizarre.

At the same time, you see the effect of this. Maybe the first of these automated sequences, you received them as an executive. “Oh look, it’s diligent follow-up. They’re following up.”

Stop customers from experiencing this kind of following-up

And you get those today, and I think my spam folder is filled with hundreds and hundreds and hundreds of, “Hey, did you get my last email?”

So, the rant of, “Stop. We must stop this in sales. It’s not working. It is not going to work. It’s going downhill, and it’s going to have to continue to go downhill.”

That developed into the “hold the hustle” thesis, and that’s gotten a huge response. I think everyone intuitively got that.

And we were able to, luckily, kind of articulate something that many people were feeling of why the tools that they were told to develop, and employ is just not driving at anything that even came close to building trust and empathy.

Biggest influence on the buying journey

Brian:    Yeah, and as part of my work interviewing customers, it’s surprising how little impact marketing has in their journey, regarding the marketing of the vendor, and how they’re learning in the process.

But, what a difference the salesperson makes in the customer experience and in terms of building trust, in terms of the customers want to know the sales rep is their advocate.  They want to know they’re talking to them straight. They’re not pitching to them.

Brian: So, as you’ve done your own outreach, can you share any stories, or any stories of people who’ve held the hustle, and what they’ve seen? If they were doing it one way and any changes you’ve noticed, or what’s been the results?

Buyers want you to journey along with them  

Steve: If you look at what buyers are looking for, it’s that person to go along with them on a journey and challenge them, educate them, make them squint, turn their head sideways and look at a problem in a new light. It’s that; that’s what people want.

The facts and information are all out there. What you’re looking for as a buyer is not that. You can get that. You can go google something, you can find any facts and information.

• What you want is the “So, what?”


• What does it mean?


• What are the challenges?


• Where is it going to work?


• Where is it not going to work?

And the salespeople who have been able to say, “No. That is my job. My job is to challenge people.” And they go deep on customer problems.

They try and understand that aspect of the customer’s world better than the customer, and they focus in on the right question.

When you get hit with that question and, “Huh, I didn’t think about it that way. Okay, now I’m listening.”

Now there’s an opportunity for us to talk because I didn’t think about my world in the way that you just asked about it. And so now the light bulb’s gone off, and I realize that there’s something more for me to learn.”

Moving the trust bar forward

That’s when that bar of trust starts to move forward, and it’s the sales reps that come at it that way and find those opportunities to say:

“Is something going on in your world, Brian? You’re probably thinking about it this way, and I’m going to push you to think about it that way and here’s why and here’s a story, and you’re going to be maybe a little uncomfortable with the story.  However, it’s going to give you some insight