B2B teams have more channels, more tools, and more “signals” than ever.

And buyers are tuning them out harder than ever.

Not because buyers hate marketing.

Because they hate being treated like a target.

This is the core problem: modern GTM systems are optimized for activity — touches, sequences, attribution — while buyers are trying to do something else entirely: reduce risk and make a safe decision.

That is why trust and empathy are not “soft skills.” They are conversion infrastructure.

In this conversation, I interviewed Steve Woods (@stevewoods), founder and CTO at Nudge, about what it takes to build real B2B relationships in a world full of automation, hustle culture, and buyer skepticism.

We talk about why automated sequences are losing effectiveness, why buyers want a guide instead of a pursuer, how trust affects deal progress, and how sales and marketing teams can use automation to support human connection instead of replacing it.

Author’s note: This transcript is edited for clarity and readability.

Steve Woods is the founder and CTO of Nudge. Before Nudge, Steve co-founded Eloqua, one of the early leaders in marketing automation.

Steve has spent his career thinking about how sales and marketing teams use data, relationships, trust, and timing to help buyers move forward.

00:00 Introduction to Steve Woods and Nudge

You build trust and empathy by helping buyers make progress before asking them to buy.

That means maintaining context, offering useful next steps, and trading self-promotion for perspective. Automation can support the research, timing, and relationship tracking. It cannot replace the human work of building trust.

“The core was getting the trust and the relationships.” — Steve Woods

“Buyers are all about developing an understanding and guiding themselves down a journey.” — Steve Woods

“You can’t automate empathy. You can’t automate trust.” — Steve Woods

“You haven’t asked first. You’ve given first.” — Steve Woods

“That’s not a give. That’s an ask.” — Steve Woods

It is tempting to blame channels.

But the real issue is behavioral.

Buyers have learned to protect themselves from noise. They have been trained by years of spammy follow-up, vague “checking in,” and fake personalization.

So they do what rational people do. They ignore you until they need something specific.

Trust becomes the differentiator because it reduces buyer risk:

That is the frame for everything below. Not “how to nurture.” Not “how to get replies.”

How to become safe to engage.

If you found this episode helpful, subscribe to the B2B Roundtable Podcast wherever you listen.

Brian: So, Steve, tell us a little bit about your background and what inspired you to start Nudge.

Steve: Sure thing. You and I have known each other, obviously, for a long time. A few decades.

My history prior to Nudge was Eloqua in the marketing space. Obviously, that’s a space you’re very familiar with. You work a lot with marketers.

At Eloqua, we were able to see this wonderful transition as marketing went from kind of an arts-and-crafts discipline to a very measured lead generation and demand generation discipline that started to connect with sales.

Here are leads that are qualified. Here are leads that are interested. 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.

The core was getting the trust and the relationships, and the breadth and depth of relationships in our organization, that would then allow that deal to move 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 as a way 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 really cool, just how you took your story from where you were to what you’re doing right now.

What are some of the lessons you’ve learned about building a company now versus when you were building Eloqua, and thinking about what you’ve learned over the past decade?

Steve: I think the thing that we were lucky with more than anything at Eloqua was being part of a major change in a space.

Marketing went from unmeasured to measured, and there were all the effects 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 flow along with that river.

What we were trying to do with Nudge was 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?”

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

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

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

That’s turned out to be true, as you’re seeing the evolution of the sales space. It’s a really interesting place to find ourselves in the middle of.

Brian: Prior to us having our interview, we were just talking about some of the changes that have happened in sales, what’s been happening for our customer, and how difficult it’s gotten for people to get things done, including buying.

One of the things that got us reconnected is that I read the post you wrote about holding the hustle. What inspired you to think about hold the hustle, and how has it influenced how you do your own outreach at Nudge?

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

It’s interesting because we’re really working in this space of sales. We spent a lot of time and developed a series called “How I Buy,” which interviews buyers on how they actually go about buying.

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 guiding themselves down a journey. They selectively bring in salespeople when they need some deeper points of view, and they really want them to be thoughtful co-conspirators on a journey.

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

It was all hustle, hustle, hustle.

It was bizarre to look at these and realize they were attempting to describe the same animal.

At the same time, you’re seeing the effect of this. Maybe the first of these automated sequences you received as an executive felt like diligent follow-up. “Oh look, they’re following up.”

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

So the rant was, “Stop. We just have to 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 got a huge response.

I think everyone intuitively got that, and we were able, luckily, to articulate something that a lot of people were feeling: why the tooling they were told to develop and employ is just not driving anything that even came close to building trust and empathy.

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

But what was particularly insightful is what a difference the salesperson makes in the customer experience, in terms of building trust. 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.

As you’ve done your own outreach, can you share any stories of people who’ve held the hustle and what they’ve seen? If they were doing it one way and changed, what have you noticed? What’s been the result?

Steve: Absolutely.

If you look at what buyers are looking for, it is 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.

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 Google something and 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?

The salespeople who have been able to say, “No, that is my job. My job is to challenge people,” go deep on customer problems.

They try to understand that aspect of the customer’s world better than the customer. They focus on the right question.

When you get hit with that question of, “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 own world in the way that you just asked about it.

Now the light bulb has gone off, and I realize that there’s something more for me to learn.

That’s when that bar of trust starts to move forward.

It’s the sales reps who come at it that way and find 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. Here’s why. Here’s a story, and you’re maybe going to be a little uncomfortable with the story.”

But it’s going to give you some insight that you wouldn’t have gotten just doing a Google search.

Brian: I like the word insight. As I was listening to you, I thought that everything you were saying is helping your customer have that insight and find that aha.

Because if we’re going to drive change, and that’s what people are doing when they decide to solve a problem or buy something, change is hard.

Not only that, helping other people experience change is even harder.

So how do we do that?

It sounds like a lot of the work you’ve been doing has been connecting the dots, helping people understand the relationships, and helping them go through that journey.

As you think of automation, and you’ve been a part of this space for a long time, how do you see empathy and automation fitting together in how sales and marketing do outreach today?

Steve: I think that is the key question.

I think the answer is a little bit easier than it would seem, because the simple version of the answer is: you can’t automate empathy. You can’t automate trust.

But there’s a lot of background work that goes into finding the opportunities to say, “Oh, there’s a chance here that I can add a little bit of value to your world that you wouldn’t have expected.”

To do that, I need to understand my world. I need to understand you, your history, your business, and what’s going on right now.

Then I need to put those two together and insert a point of view in the conversation.

Doing all that background research to say, “What’s happening right now with you, your journey at large, and your journey with my business specifically?” and then mapping that out to a point of view can be done through a lot of automation and AI.

The conversation — “Hey Brian, saw this, thought that, here’s what’s going on, here’s how you might want to think about it” — that’s a very human thing to do.

Automation can put enough of it on a silver platter to say, “Here’s where Brian’s at, and these next steps on the journey might make sense based on all of this history and where he’s at right now today.”

That can be facilitated by automation. It’s a lot of research and grunt work, and it can be optimized a lot better to tee up those silver platter moments.

Brian: I think that really is the tricky thing, right?

It’s pulling together the right data and then also having empathy, which gives you that intuition or insight to ultimately say, “Okay, emotionally, I’ve got more emotional intelligence of what the situation needs, what this person is looking for, and what they’re experiencing.”

How are they going to have that next conversation? What would be useful to share with them at this point in time?

Let’s get really practical. Can you talk about any actionable tips or advice you’ve learned through your own experience that could help sellers do better outreach right now?

Steve: Absolutely.

I think the easiest step for anyone who’s trying to build relationships is, quite simply, to look at those relationships and ask, “Where am I losing touch?”

Most people don’t do that.

You have the first conversation. If it goes to a deal, great. Ninety percent of them don’t, and they just drop off.

The best reps used to do this manually with Excel spreadsheets.

One of the things we focus on with Nudge is where you can say, “Look, just make sure I’m in touch with these people every three months. That’s it. I just need to reach out.”

That puts a floor on your relationship building.

But then the next point is, okay, I now need to develop this logical next step for where that person is on the journey they’re mapping out.

So I need to understand what’s going on in their world.

What’s happening with their company? What are the new recent events that have happened? Have there been any executive changes? Where are they on their journey with my organization?

This is sort of an advancement of the digital body language concept that you and I chatted about over the last decade.

Where are they? What have they done? What have they looked at? Have they used a free trial? Did they get value out of it? Where are they on that journey?

Given all of those things, what can I nudge them to do next?

Can I say, “You’re probably here, and you’re probably thinking this. But if you just did this one little thing, thought about it in a different way, or looked at a data set I’m going to send over to you, your perspective would evolve.”

It’s not a sales pitch. It’s not, “Hey, let’s do a one-hour sales call.”

It’s, “Let me show you a new perspective that you might appreciate.”

If you can do that and you can guide them along this journey, what you’re doing is pushing them forward on a journey, but you’re also building trust.

You haven’t asked first. You’ve given first.

In doing so, you’ve built those little tiny nuggets of trust that eventually will guide you to be able to say, “Hey, let’s do something here. I think you’ve gone down this journey, and your next step on the journey actually is to become a customer of ours. Here’s what that would look like. We’ve built all this trust. Let’s make this happen.”

Brian: I love that. If our audience were just to take those insights and apply them, I think it would make a difference.

As I was listening to you, there are two ways of building relationship. One is like we’re doing: having a conversation, dialoguing together.

The second way is reciprocal altruism. What it really means is we give something of value to someone without expecting anything in return. It doesn’t feel like there’s something attached to it.

That really is the trick: to know it isn’t about being tricky. It’s focusing on, “My intention is to help this person. To do that, I need to understand. To do that, I need to understand where we are in our relationship.”

As you talked about, where they’re at in their journey, what are the questions they’re dealing with? What might they be thinking about? What might they be feeling at this moment?

So that I can actually help them and present what would be useful at that point in time.

Steve: Yeah. It’s interesting because if you extend that train of thought, you get this really interesting challenge for the rest of the world, the world of marketing.

Marketing, for the last decade, has not focused as much as it could on those value-added nuggets that I as a salesperson can give to you when the moment is right.

When you’re at that point on the journey, what is my give?

If a sales team doesn’t have those gives, then they’re kind of stuck with, “Hey, let’s set up a 60-minute sales call.”

Well, that’s not a give. That’s an ask. That’s a big ask. So the answer is no.

The evolution of marketing that we’re seeing today in some of the top organizations is to be able to come up with those things that are actual gives.

They’re useful information. They’re useful data sets. They’re useful documents, trials, or experiences.

They’re not traps.

They’re not a half thing where you need to take a sales call to get the other half thing.

They’re actual gives that build trust and move a buyer along the relationship.

It’s a really interesting challenge for marketing, and some marketers are getting into it with quite a bit of gusto.

Brian: I think that is difficult unless someone is able to think beyond, “My role as a marketer is to generate a lead or get an MQL.”

Some people have called it full-funnel marketing. Other people have called it revenue marketing. I think it’s really about customer marketing and customer experience.

It starts with the first touch and continues throughout.

It’s having marketers see beyond that, because a lot of the trust building is happening through that human being — the sales rep or the sales development rep.

What can I do to equip them so that every touch they have with that customer is a positive experience and is helpful?

That’s really the best brand building.

All the other things that we want to have in marketing — brand, conversion, more opportunities, more pipeline — it all starts with adding value.

To do that, it requires us to maybe take the pedal off trying to focus on conversion all the time.

Steve: Yeah. I think the focus on conversion kind of made sense in the world that we were in 10 years ago, where a deal, if I can overgeneralize, was a big moment in time.

Brian: Yeah.

Steve: A customer went from not a customer to a big three-year contract, multiple hundred thousand, now they are a customer. Over the wall to customer success, out of the world of sales.

That’s not the reality now.

Most buying journeys look more like a ramp than a step function.

You come in, maybe you’re on a trial product, maybe you’ve got one team, maybe you’ve got a month-to-month license, and then your experience grows and evolves and builds from there as you achieve success and go down that journey’s pathway.

You ultimately become a very successful, large enterprise client.

But it’s not a step function. It’s a growth process.

If you, as a marketing team, are thinking forward like that, you’re giving your sales teams — whether you call them sales teams, account farmers, customer success reps that have revenue responsibility, whatever they look like, whatever business card they hold — the tooling to help guide buyers along that journey to become more and more deeply ingrained with your organization, more trusting, and more successful.

Brian: Well Steve, thank you. This has been fun. What’s the best way for readers and listeners to get in touch with you?

Steve: I exist on all forms online. [email protected]. You should be able to find me on LinkedIn or Twitter. And nudge.ai is our website. So if you can’t find me, you’re not trying hard enough.

Brian: Thanks again.

Steve: Thank you, Brian.