The LinkedIn Outreach Strategy That Actually Starts Real Conversations - Jack Hayes

March 15, 2026  by Ewell Smith

Most people treat LinkedIn like a cold email machine. That’s why their outreach gets ignored.  In this episode of the Close The Deal Podcast, Jack Hayes shares a completely different approach—one that starts with curiosity, feedback, and real conversations instead of a pitch.

Most LinkedIn outreach fails. Here’s why this one works.


Listen to the Close The Deal Podcast:

What You Will Learn



  • Why traditional LinkedIn outreach fails
  • The psychology behind asking for feedback instead of pitching
  • How to structure LinkedIn messages that get responses
  • Why Gen Z entrepreneurs are blending old-school sales with modern tools
  • How automation and AI can support better prospecting


About the Guest


Jack Hayes is the founder of Profit Jack Enterprises, a B2B growth partner helping companies generate leads through LinkedIn, cold email, and tech-driven outreach systems.


Jack specializes in helping consultants, founders, and private equity professionals scale their client acquisition using modern AI growth systems combined with relationship-based outreach. Known for his unique LinkedIn feedback strategy, Jack focuses on helping businesses create genuine conversations that lead to real opportunities.


Why Most LinkedIn Outreach Fails


LinkedIn has become one of the most powerful platforms for B2B sales.

But there’s a problem.

Most people use it the wrong way.


If you’ve ever opened your LinkedIn inbox, you know exactly what this looks like. Someone connects with you… and five seconds later you get a pitch.

“Hi, great to connect. Here’s what I do…”


It’s predictable. It’s impersonal. And it rarely works.

That’s why Gen Z entrepreneur Jack Hayes built a completely different approach.


Instead of pitching prospects, he starts conversations.

And it starts with one simple shift.

Ask for feedback.


The Psychology Behind Asking for Feedback



Most sales outreach focuses on positioning the sender as the expert.

But Jack flips that approach.


Instead of trying to prove expertise immediately, he activates the expertise of the person he’s reaching out to.


When you message someone and ask for their feedback, several things happen instantly:


First, the conversation becomes collaborative.


Second, you respect the experience of the person you're reaching out to.

Third, you remove the defensive barrier people naturally build when they expect a sales pitch.


This small shift changes the entire dynamic of the conversation.

Instead of feeling sold to, the other person feels valued.

And that dramatically increases the likelihood they respond.


Why LinkedIn Is Built for This Strategy


LinkedIn isn’t like other social platforms. The platform itself is built around connections.


Not followers.

Connections.


That small detail reveals the real intent behind LinkedIn: professional conversations.


Yet most outreach strategies treat LinkedIn like an automated cold email machine.


Mass messages.

Generic pitches.

Volume over value.


Jack’s approach brings the platform back to what it was originally designed for: professional dialogue.


The Simple Outreach Framework


The strategy itself is surprisingly simple.

Step one is sending a connection request.


But instead of immediately pitching, the first message focuses on context.

You briefly explain:


• The problem you solve
• Who you help
• A quick example or proof


Then comes the key element.

You ask for feedback.

Not a sales call.

Not a meeting.

Feedback.


For experienced founders and executives, this immediately triggers curiosity. Their expertise is being acknowledged.


And that makes them far more likely to engage.


Automation Without Losing the Human Touch


Automation tools have become common in LinkedIn prospecting.

But many companies misuse them.


Instead of helping conversations happen faster, automation becomes a spam machine.

 

Jack’s rule is simple:

Automation should only support human conversations.


That means limiting follow-ups, avoiding aggressive message sequences, and always making sure messages feel like they came from a real person.

When automation respects the relationship instead of replacing it, it becomes a powerful growth tool.


The Real Meaning of Closing the Deal


When asked what “closing the deal” means, Jack gives a refreshingly direct answer.


Cash collected.


Not promises.

Not contracts.

Not performance projections.

Cash collected.


It’s a simple reminder that sales ultimately comes down to results. Conversations, relationships, and outreach strategies all matter—but at the end of the day, businesses run on revenue.


The Lesson for Entrepreneurs


The biggest insight from this conversation is simple.

People don’t want to be pitched.


But they’re always open to a conversation.

When you approach outreach with curiosity instead of persuasion, something interesting happens.


People respond.

Conversations start.

Opportunities open.


And sometimes, that single conversation leads to the deal.


Episode Summary


In this episode, Jack Hayes shares a modern approach to LinkedIn outreach built around asking for feedback instead of delivering sales pitches. By activating the prospect’s expertise and focusing on conversation rather than persuasion, founders can dramatically increase response rates and build stronger B2B relationships.


Key Questions This Episode Answers


  • Why do most LinkedIn outreach messages fail?
  • How can entrepreneurs generate B2B leads without sounding like a salesperson?
  • What is the feedback-driven outreach strategy on LinkedIn?
  • How should founders use automation without damaging their reputation?
  • What role does Gen Z play in reshaping modern sales strategies?


Top 3 Jack Hayes Mindset Quotes:


“Instead of pitching someone, ask for their feedback.”


“LinkedIn is built on connection, but most outreach removes the connection.”


“Closing the deal means cash collected.”



Frequently Asked Questions

  • Why do most LinkedIn sales messages fail?

    Most outreach fails because it immediately jumps into a sales pitch instead of starting a conversation. People naturally ignore messages that feel automated or self-focused.

  • What is feedback-driven outreach?

    Feedback-driven outreach involves asking prospects for their perspective on a problem or idea instead of pitching them a product or service.

  • Can LinkedIn automation still work?

    Yes, but it should support genuine conversations. Over-automated messaging sequences often damage trust and response rates.

  • What does “closing the deal” really mean?

    According to Jack Hayes, a deal is only closed when the money is collected. Revenue—not promises—is the real measure of success.

Close The Deal Takeaway


The biggest lesson from this conversation is simple.


People respond to curiosity.


Not pitches.


When you ask for feedback, you invite someone into a conversation instead of pushing them into a sales process.


That one shift can open doors, build relationships, and ultimately lead to more deals.



And that’s exactly the kind of practical insight we aim to share on the Close The Deal Podcast.

If you're finding this helpful, you may enjoy 40 Top Dale Carnegie Quotes


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Ewell Smith, host of the Close The Deal Podcast, discussing sales systems and revenue growth

About the Author Ewell Smith is the publisher of CloseTheDeal.com, host of the Close The Deal Podcast, and author of Your First Franchise Roadmap. He interviews franchisors, founders, and sales and marketing leaders to help franchise owners and candidates drive more revenue and find the right opportunity. His work focuses on practical franchise strategy, the right mindset, and helping people close the deal on their next chapter.

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