Growing B2B Sales with Trust and Empathy interview with Steve Woods, Founder & CTO at Nudge

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’s why trust and empathy aren’t “soft skills.” They’re
conversion infrastructure.


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


Author’s note: This transcript is edited for clarity and
readability.
Quick Answer: How Do You Build Trust and Empathy in B2B Sales?

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


That means: maintain context, give useful “next steps,” and trade
self-promotion for perspective. Automation can support the
research and timing. It cannot replace the human work of
building trust.
Key Takeaways


Trust moves deals. “Activity” does not.

Buyers want a guide, not a pursuer.

Automated sequences are decaying because they strip context.

The best outreach is a give, not a disguised
ask.

Your system should surface relationship risk (lost touch,
stalled progress), not just track touches.

Why Buyers Are Tuning You Out

It’s tempting to blame channels.


But the real issue is behavioral.


Buyers have learned to protect themselves from noise. They’ve
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:


Risk of wasting time

Risk of looking foolish internally

Risk of choosing the wrong vendor

Risk of being pressured into the wrong timing



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


How to become safe to engage.
The Interview Brian: What inspired you to start Nudge?

Steve: You and I have known each other for a
long time. A few decades. My history before Nudge was Eloqua in
the marketing space.


We saw marketing transition from an arts-and-crafts discipline
into a measured lead generation and demand generation engine that
started to connect with sales.


That was remarkable.


But looking over the fence at sales, we realized the next step
was the core of getting deals done.
Steve: Building trust and relationships is the core

The core was building trust and relationships, and the breadth
and depth of those relationships within our organization, that
would allow the deal to move forward.


Trust and empathy had to be developed, and ultimately the deal
would be closed based on those relationships.


So we decided to tackle relationship intelligence: understanding
where trust is being built, where empathy is being built, and how
you make a sales team more effective by focusing efforts on the
right initiatives.
Brian: What growth lesson did you learn from Eloqua?

Steve: We were lucky to be part of a major
change. Marketing went from unmeasured to measured.


With Nudge, we tried to be proactive: what dominant theme will
shape sales for the next decade?


It became clear that relationships, trust, empathy were the core
thing. And it was unmeasurable. It was intuitive.
Steve: Deal slippage is relationship slippage

Every sales leader, when you talk about deal progress and
forecast and slippage, it’s about relationships and trust. But
it’s not measurable. It’s self-reported by sales reps who often
have happy ears.


We thought: if we can put measurement around trust, empathy, and
relationships, then build tooling to steer effort, we can be part
of a meaningful transition.
Why “Hustle” Collapses Trust Brian: What inspired you to write
about holding the hustle?

Steve: It stemmed from a rant.


We spent time interviewing buyers about how they buy, and
salespeople about how they sell. It was Mars and Venus.


Buyers want thoughtful co-conspirators on a journey. They
selectively bring in sales when they need deeper points of view.


Salespeople talked about automation, numbers, a thousand emails a
day, “Did you get my last email?”


It was bizarre to realize they were describing the same animal.


Early sequences felt like diligence. Now they feel like spam.


So the rant was: “Stop. We must stop this in sales. It’s not
working. It’s going downhill.”


That became the #HoldTheHustle thesis.
Buyers Don’t Need More Info. They Need Meaning Brian: What
makes a difference in the buyer journey?

The salesperson often matters more than marketing in the buyer’s
lived experience.


Buyers want to know the rep is their advocate, talking straight,
not pitching.
Steve: Buyers want you to journey along with them

Buyers want someone to go along with them on a journey and
challenge them, educate them, and help them see the problem
differently.


The facts are out there. Buyers can Google facts.


What they want is:



So what?


What does it mean?


Where will this work?


Where will it fail?



When a rep asks a question that makes the buyer pause and think,
trust starts moving forward.
Steve: The trust bar moves when you create insight

“You’re probably thinking about it this way. I’m going to push
you to think about it that way. Here’s why. Here’s a story. It
might make you uncomfortable. But it’ll give you insight you
wouldn’t get from a search.”
Empathy and Automation: Where They Actually Fit Brian: How do
empathy and automation fit together?

Steve: You can’t automate empathy. You can’t
automate trust.


But you can automate the background work that makes empathy
possible: understanding your world, understanding the buyer’s
world, and teeing up the moments where a human can add value.


The human part is the conversation:


“Saw this, thought this, here’s a perspective you might
want to consider.”


Automation can put enough on a silver platter to guide those
“right moment” conversations.
3 Practical Steps to Build and Grow Relationships Step 1:
Identify where you’re losing touch

Steve: Look at your relationships and ask,
“Where am I losing touch?” Most people don’t do this.


You have a first conversation. If it becomes a deal, great. But
90% don’t, and they drop off.


The best reps used to manage this manually in spreadsheets.


At minimum, put a floor under relationship building: stay in
touch on a simple rhythm (for example, every 90 days) with people
who matter.
Step 2: Define the next step that helps them on their journey

Now you develop the logical next step based on where they are.


You need context:


What’s happening in their company?

What recent events occurred?

Executive changes?

Where are they in their journey with your organization?



This is the evolved version of “digital body language,” but
grounded in reality, not vanity engagement.
Step 3: Nudge them forward with a give, not a pitch

The next step is a nudge: “You’re probably here. You might be
thinking this. If you considered this dataset, this perspective,
this story, your view would evolve.”


Not a sales pitch.


Not “Let’s do a one-hour call.”


A give that builds trust first. Then, later, you’ve earned the
right to ask.
The Hidden Challenge for Marketing: Do You Have Any “Gives”?

Steve: If sales doesn’t have real gives, they’re
stuck with big asks: “Let’s schedule a 60-minute call.”


That’s not a give. That’s a tax.


The best orgs build actual gives:


useful datasets

helpful documents

experiences that reduce buyer risk

insight that helps internal alignment



Not traps. Not half-assets that require a call to unlock the
other half.


Real gives create real trust.
Hard Truth: Trust Is Your Only Sustainable Conversion Strategy

Buyers don’t hate follow-up.


They hate follow-up that has no point.


They hate being chased with zero context.


They hate “personalization” that’s just a variable token stuffed
into a template.


Trust is built when your system helps buyers think, not
when it tries to make them act.


If your GTM motion is built on hustle, your buyers will
experience you as risk.


And rational buyers don’t buy risk.
Bottom Line

Empathy is not soft. It’s operational.


If your system can’t preserve context, equip humans with useful
gives, and support buyer progress, your “optimization” will just
create more noise faster.


Stop trying to out-automate buyer skepticism.


Build trust like it’s a revenue system. Because it is.
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