Founders. VPs. Operators. Safety leaders. People actually running businesses.
When I reach out, not to sell, but to ask a few thoughtful questions, the response rate has been surprisingly high.
Not because of a clever tactic.
Not because of automation.
Not because of AI.
But because most outreach today skips the one thing serious operators still value.
Context.
We broke B2B outreach by trying to scale it too fast
Somewhere along the way, outreach turned into volume theater.
More messages.
More tools.
More links.
More follow-ups.
Less thinking.
Most leaders can spot a pitch in the first sentence. Their guard goes up immediately. Even if the product is good.
That’s why you’re seeing a weird paradox right now.
Everyone says cold outreach is dead.
Yet the people doing it thoughtfully are getting replies from senior executives.
What’s actually working
After dozens of conversations across logistics, trucking, safety, and technology, a few patterns are clear.
First, people respond to curiosity, not claims.
When the message sounds like:
“I’m trying to understand what’s actually happening on the ground”
It opens doors.
Second, permission beats persuasion.
Asking “Would you be open to a few questions?” works better than explaining why you’re worth 30 minutes.
Third, async wins.
Executives don’t want another call.
Operators don’t want another demo.
They want space to respond when it fits their day.
Fourth, specificity signals respect.
When you reference someone’s role, context, or real responsibilities, it shows effort. That effort gets reciprocated.
What leaders actually want to talk about
Here’s what keeps coming up in these conversations:
• Inconsistency at scale
• The gap between leadership plans and operational reality
• Tools that exist but aren’t adopted
• Safety and compliance becoming more complex, not simpler
• Technology that promises transformation but delivers friction
None of this shows up in pitch decks.
All of it shows up in real conversations.
The mistake most companies are making
They lead with answers before earning the right to ask questions.
They push tools before understanding workflows.
They talk outcomes before understanding constraints.
They optimize for clicks instead of conversations.
And then they wonder why engagement is shallow.
A better way forward
The teams winning attention right now are doing a few simple things differently.
They listen before they explain.
They ask before they propose.
They treat outreach as research, not extraction.
Ironically, this approach scales better in the long run because trust compounds.
Final thought
The goal of outreach was never to close in the inbox.
The goal is to earn enough curiosity that a real conversation becomes inevitable.
If you’re building, selling, or leading right now, ask yourself:
When was the last time you reached out just to understand what someone is actually dealing with?
That’s where the signal is.
That’s where the opportunity is.