The Weirdest Cold Calling Trainer 📞☎️📱 | Cold Calling CAN Be Fun! | ICF Coach | Stoic | 🍍 on 🍕 is a CRIME

Cold calling sucks - but it works well.

It's the fastest way to fix pipeline issues.

If you're struggling with it, get in touch:

UK: +44 7513 624 762

Alternatively, check out my website: www.underdogsales.com
If you're really an email person try info@underdogsales.com

Sales Trainer | Cold Calling Trainer

Giulio Segantini

𝗬𝗼𝘂 𝗱𝗼𝗻'𝘁 𝘀𝘂𝗰𝗸 𝗮𝘁 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹𝗶𝗻𝗴.

You just haven't mastered the crucial part:

Handling the ridiculous amount of rejection.

Your brain takes rejection worse than physical pain.

You can either succumb to it or fight back.

Only those who fight back win.

3 simple ways to fight it:

1. Stick to clear calling blocks
At least 60 minutes, 3 times per week.

2. Practice Opener and Pitch before
The warming up will get your brain ready.

3. Find a way to consistently have fun
Laughter is nature's strongest painkiller; use it.

Don't be like Batman, who gave up here.

𝗜𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗿𝗲𝗮𝗱𝘆 𝘁𝗼 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹 𝘁𝗼𝗱𝗮𝘆, 𝗱𝗿𝗼𝗽 𝘀𝗼𝗺𝗲 𝗺𝗼𝘁𝗶𝘃𝗮𝘁𝗶𝗼𝗻 𝗶𝗻 𝘁𝗵𝗲 𝗰𝗼𝗺𝗺𝗲𝗻𝘁𝘀 👇

(𝗦𝗼𝗻𝗴𝘀 𝗼𝗿 𝘃𝗶𝗱𝗲𝗼𝘀 𝘁𝗼 𝗽𝘂𝗺𝗽 𝘆𝗼𝘂 𝘂𝗽)
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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

The Weirdest Sales Trainer ❄️📞 Making Cold Calling FUN | Pineapple on Pizza is a Crime | Fan of Stoicism

𝗜𝗳 𝗜 𝗵𝗮𝗱 𝘁𝗼 𝗺𝗮𝘀𝘁𝗲𝗿 𝗼𝗻𝗲 𝘀𝗸𝗶𝗹𝗹 𝗳𝗼𝗿 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹𝗶𝗻𝗴..

It wouldn't be objection handling, but:

Asking the right questions.

"𝘑𝘶𝘥𝘨𝘦 𝘢 𝘮𝘢𝘯 𝘣𝘺 𝘩𝘪𝘴 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯𝘴 𝘳𝘢𝘵𝘩𝘦𝘳 𝘵𝘩𝘢𝘯 𝘣𝘺 𝘩𝘪𝘴 𝘢𝘯𝘴𝘸𝘦𝘳𝘴."
- Voltaire

Statements are about you.

Questions are about the prospect.

Some of my favourites:

• What do you mean by that?
An easy way to get the prospect to talk more.

• Can you give me an example?
Another way to get talking more about problems.

• What's your favourite pizza topping?
There's no better way to become forever memorable.

𝗪𝗵𝗮𝘁'𝘀 𝘆𝗼𝘂𝗿 𝗙𝗔𝗩𝗘 𝘀𝗮𝗹𝗲𝘀 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻?

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

𝗦𝗵𝗲 𝘀𝗮𝘆𝘀: "𝗜'𝘃𝗲 𝗴𝗼𝘁 𝗮 𝗯𝗼𝘆𝗳𝗿𝗶𝗲𝗻𝗱."
 
It's like "I have a supplier", it's not over.

ACE Framework, watch:

𝗔: Accept.
"𝘐'𝘥 𝘣𝘦 𝘴𝘶𝘳𝘱𝘳𝘪𝘴𝘦𝘥 𝘪𝘧 𝘺𝘰𝘶 𝘥𝘪𝘥𝘯'𝘵"

𝗖: Consent.
"𝘊𝘢𝘯 𝘐 𝘢𝘴𝘬 𝘢 𝘥𝘪𝘳𝘦𝘤𝘵 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘢𝘵?"

𝗘: Explore.
"𝘈𝘳𝘦 𝘺𝘰𝘶 100% 𝘴𝘢𝘵𝘪𝘴𝘧𝘪𝘦𝘥 𝘸𝘪𝘵𝘩 𝘩𝘰𝘸 𝘩𝘦 𝘵𝘳𝘦𝘢𝘵𝘴 𝘺𝘰𝘶?"

"𝘐𝘧 𝘵𝘩𝘦𝘳𝘦 𝘸𝘢𝘴 𝘰𝘯𝘦 𝘵𝘩𝘪𝘯𝘨 𝘩𝘦 𝘤𝘰𝘶𝘭𝘥 𝘥𝘰 𝘣𝘦𝘵𝘵𝘦𝘳, 𝘸𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘵𝘩𝘢𝘵 𝘣𝘦?"

Sales is life, especially dating.

𝗗𝗿𝗼𝗽 𝘆𝗼𝘂𝗿 𝗯𝗲𝘀𝘁 '𝘀𝗮𝗹𝗲𝘀 𝗼𝘂𝘁𝘀𝗶𝗱𝗲 𝗼𝗳 𝘀𝗮𝗹𝗲𝘀' 𝘀𝘁𝗼𝗿𝘆.

𝗣𝗦: looking forward to the drama in the comments.

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

𝗪𝗵𝘆 𝘄𝗼𝘂𝗹𝗱 𝗮𝗻𝘆𝗼𝗻𝗲 𝘀𝗮𝗻𝗲 𝗱𝗲𝗰𝗶𝗱𝗲 𝘁𝗼 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹?

It definitely doesn't help your:
1. Peace
2. Sleep
3. Therapy bill
4. Liver health

But it does make you:
1. Richer
2. Disciplined
3. Mentally tough
4. Resistant to rejection

In my first job I was cold calling on day one.

I didn't love it, but my manager made me do it.

12 years later, I built a massive business and brand.

𝗪𝗵𝘆 𝗱𝗼 𝗬𝗢𝗨 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹?

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

𝗬𝗼𝘂𝗿 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹 𝘀𝘁𝗮𝗿𝘁𝘀 𝗼𝗿 𝗱𝗶𝗲𝘀 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿 𝗼𝗽𝗲𝗻𝗲𝗿.

Most salespeople get it wrong:

1. "Is this John?"
Tells them right away you don't know them.

2. "My name is ... from ..."
Unless you're Elon Musk from Tesla, no one cares.

3. "How are you doing today?"
Unless you sound REALLY genuine, it's a waste of time.

Instead, go directly to the point:

"𝘎𝘰𝘰𝘥 𝘮𝘰𝘳𝘯𝘪𝘯𝘨, 𝘑𝘰𝘩𝘯, 𝘺𝘰𝘶 𝘸𝘦𝘳𝘦𝘯'𝘵 𝘦𝘹𝘱𝘦𝘤𝘵𝘪𝘯𝘨 𝘢 𝘤𝘰𝘭𝘥 𝘤𝘢𝘭𝘭, 𝘣𝘶𝘵 𝘪𝘵'𝘴 𝘢 𝘸𝘦𝘭𝘭-𝘳𝘦𝘴𝘦𝘢𝘳𝘤𝘩𝘦𝘥 𝘰𝘯𝘦"

It works because:
1. Straight to the point
2. Seeks permission
3. Trigger curiosity

Batman may not like it, but it works.

𝗔𝗻𝘆𝗼𝗻𝗲 𝘄𝗶𝘁𝗵 𝗮𝗻 𝗲𝘃𝗲𝗻 𝗯𝗲𝘁𝘁𝗲𝗿 𝗼𝗽𝗲𝗻𝗲𝗿?

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

𝗬𝗼𝘂𝗿 𝘀𝗮𝗹𝗲𝘀 𝗽𝗶𝘁𝗰𝗵 𝗶𝘀 💩

This is what it sounds like 69%+ of the time:

"𝘞𝘦'𝘳𝘦 𝘢𝘯 𝘪𝘯𝘯𝘰𝘷𝘢𝘵𝘪𝘷𝘦 𝘤𝘰𝘮𝘱𝘢𝘯𝘺 𝘸𝘪𝘵𝘩 𝘪𝘯𝘤𝘳𝘦𝘥𝘪𝘣𝘭𝘦 𝘦𝘹𝘱𝘦𝘳𝘵𝘪𝘴𝘦 𝘢𝘯𝘥 𝘰𝘶𝘵𝘴𝘵𝘢𝘯𝘥𝘪𝘯𝘨 𝘳𝘦𝘴𝘶𝘭𝘵𝘴"

The problem? 
Everyone says the same BS.
You'll sound more boring than white rice.

Instead, you should always lead with their problems:

"𝘞𝘦 𝘴𝘱𝘦𝘢𝘬 𝘵𝘰 𝘰𝘵𝘩𝘦𝘳 {𝘫𝘰𝘣 𝘵𝘪𝘵𝘭𝘦}, 𝘵𝘩𝘦𝘺 𝘸𝘰𝘳𝘬 𝘩𝘢𝘳𝘥 𝘣𝘶𝘵:
1. 𝘚𝘵𝘪𝘭𝘭 𝘧𝘢𝘤𝘦 {𝘱𝘳𝘰𝘣𝘭𝘦𝘮 1}
2. 𝘰𝘳 𝘢𝘭𝘵𝘦𝘳𝘯𝘢𝘵𝘪𝘷𝘦𝘭𝘺 {𝘱𝘳𝘰𝘣𝘭𝘦𝘮 2}
𝘞𝘩𝘪𝘤𝘩 𝘭𝘦𝘢𝘥𝘴 𝘵𝘰 {𝘤𝘰𝘯𝘴𝘦𝘲𝘶𝘦𝘯𝘤𝘦}.

𝘈𝘳𝘦 𝘺𝘰𝘶 𝘰𝘯𝘦 𝘰𝘧 𝘵𝘩𝘦 𝘭𝘶𝘤𝘬𝘺 𝘰𝘯𝘦𝘴, 𝘰𝘳 𝘪𝘴 𝘵𝘩𝘪𝘴 𝘳𝘦𝘭𝘦𝘷𝘢𝘯𝘵?"

Now you speak their language. 
You're not a salesperson - you're someone who *gets it*.  

Still pitching like Jordan Belfort? 
That's why you hear the beep sounds...

𝗜𝗳 𝘆𝗼𝘂 𝗱𝗿𝗼𝗽 𝘆𝗼𝘂𝗿 𝗽𝗶𝘁𝗰𝗵 𝗯𝗲𝗹𝗼𝘄, 𝗜'𝗹𝗹 𝗿𝗮𝘁𝗲 𝗮𝗻𝗱 𝘂𝗽𝗴𝗿𝗮𝗱𝗲 𝗶𝘁 👇🏻

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

The Weirdest B2B Sales Trainer ❄️📞 Making Cold Calling FUN | Pineapple on Pizza is a Crime | Fan of Stoicism

𝗧𝗵𝗲𝗿𝗲'𝘀 𝗮𝗻 𝗲𝗽𝗶𝗱𝗲𝗺𝗶𝗰 𝘀𝗽𝗿𝗲𝗮𝗱𝗶𝗻𝗴 𝘁𝗵𝗿𝗼𝘂𝗴𝗵 𝘀𝗮𝗹𝗲𝘀 𝘁𝗲𝗮𝗺𝘀...

Over half of them are trapped in:

A job with awful conditions.

The typical stories:
1. Ego-maniac leadership
2. Absolutely no training or coaching 
3. Calling leads older than my grandma
4. Commissions that couldn't feed a chihuahua

Sales is hard: at least do it for the bloody right company!

And yet so many salespeople are scared of change.

Therefore, they stay in awful jobs and complain.

The hard truth? They deserve it.

Sales is about being proactive.

Not sitting on your ass.

Waiting for miracles.

Do you want a better job?

• Cold call hiring managers
• Send them DMs on LinkedIn 
• Network actively with your peers
• Apply your sales skills to job hunting

If you don't, you probably deserve where you are.

That being said, if you're really struggling...

You can speak to my dear friend Anca.

She's a recruiter and career coach for salespeople.

A picture of us in Milan today as proof I have real friends.

𝗗𝗼 𝘆𝗼𝘂 𝘁𝗵𝗶𝗻𝗸 𝘆𝗼𝘂'𝗿𝗲 𝗶𝗻 𝗮 𝗴𝗿𝗲𝗮𝘁 𝗷𝗼𝗯 𝗮𝗹𝗿𝗲𝗮𝗱𝘆?

𝟲𝟵𝗞 𝘀𝗮𝗹𝗲𝘀𝗽𝗲𝗼𝗽𝗹𝗲 𝘄𝗶𝗹𝗹 𝗻𝗼𝘁 𝗰𝗮𝗹𝗹 𝘁𝗼𝗱𝗮𝘆, 𝗮𝘀 𝗶𝘁 𝗶𝘀 "𝗕𝗹𝘂𝗲 𝗠𝗼𝗻𝗱𝗮𝘆".

I'm calling it International Cold Calling Day instead.  

Why on the most depressing day of the year??

Not because cold calling is depressing (although it is).
Because real cold callers don't care about the mood.
We will do what needs to be done.

I kept track of my last 200 days:
• Days I genuinely felt like calling: 11
• Days I got it done anyway: 189
• Days I regretted doing it: 0

Success in cold calling is about discipline.

It's about saying: F*ck the mood, follow the plan.

And,  Blue Monday has three advantages:
• Competition: Over 40% of sellers skip Mondays
• Pickup Rates: Less competition = more conversation 
• Energy: You will out when everyone else is depressed

Therefore, today:
1. Park your excuses
2. Draw up your call list
3. Speak to at least 5 prospects (better if 10 ;)

Prove that the most depressing day won't stop you.

Then you can congratulate yourself.

𝗗𝗿𝗼𝗽 𝗮 📞 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗺𝗮𝗸𝗶𝗻𝗴 𝗰𝗮𝗹𝗹𝘀 𝘁𝗼𝗱𝗮𝘆.  

𝗧𝗵𝗲𝗻 𝗹𝗲𝗮𝘃𝗲 𝗮 𝗰𝗼𝗺𝗺𝗲𝗻𝘁 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝗪𝗢𝗥𝗦𝗧 𝗼𝗯𝗷𝗲𝗰𝘁𝗶𝗼𝗻 𝘆𝗼𝘂 𝗳𝗮𝗰𝗲𝗱, 𝗮𝗻𝗱 𝗜'𝗹𝗹 𝗿𝗲𝗽𝗹𝘆 𝘄𝗶𝘁𝗵 𝗵𝗼𝘄 𝗜'𝗱 𝗵𝗮𝗻𝗱𝗹𝗲 𝗶𝘁.

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Follow and 🔔 for daily (weird) sales content:  Giulio Segantini

𝗧𝗵𝗲 𝗺𝗼𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 𝗽𝗮𝗿𝘁 𝗼𝗳 𝘁𝗵𝗲 𝗰𝗼𝗹𝗱 𝗶𝘀 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗼𝗽𝗲𝗻𝗲𝗿.

And it's not objection handling either, but:

Your Sales Pitch.
Poor reps pitch features.
Decent reps pitch benefits.
Great reps pitch on problems
.Excellent reps pitch on very specific problems.

Below is a step-by-step guide on crafting a great pitch.

A great pitch will turn 30%+ of your calls into conversations
.Once you have a great pitch, all you need is a great list.

However, I'll let FullEnrich take care of that.

.𝗗𝗼 𝘆𝗼𝘂 𝗮𝗴𝗿𝗲𝗲 𝘁𝗵𝗮𝘁 𝘁𝗵𝗲 𝗽𝗶𝘁𝗰𝗵 𝗶𝘀 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁?

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Follow and 🔔 for daily (weird) sales content: Giulio Segantini

The Perfect Pitch

Alan Ruchtein

CEOs: Broken pipeline & poor performer sales reps? I fix both for you in <60 days. You’ll hate how fast it works. | Modern Seller Program Founder

Your ability to book meetings, negotiate, and close deals with potential clients will determine how far you’ll thrive as a sales rep and leader.

This will allow you to:

📈 Build a career
📈 Hit your quotas
📈 Get recognition
📈 Get a promotion
📈 Get better offers
📈 Land sponsorships

However, booking meetings and closing deals it’s harder than ever:

❌ Prospects don’t return your calls
❌ Prospects don’t stop ghosting you
❌ Prospects don’t answer your emails
❌ Prospects don’t trust you as a seller
❌ Prospects don’t believe in your offer 
❌ Prospects don’t accept your LinkedIn Invite

All of these makes you feel miserable

You feel your manager’s pressure on your shoulder

And you start thinking that sales might not be for you.

Do you relate with this? Because I do - I’ve been there

This happens because the “old way” of doing sales doesn’t work anymore.

Sending 1000s of generic emails and praying they get back to you will kill your sales career.

Now, imagine having a proven system that allows you to systematically:

✅ Book more meetings
✅ Handle all the objections
✅ Move deals through the pipe
✅ Close higher tickets in less time
✅ Run discovery and demo calls like a pro

And, hitting your sales quota.

Wouldn't this be the scenario you would like to be in?

The good news - I can help you get there with:

➝ My weekly Newsletter with actionable sales tactics
➝ My daily sales practical examples in my Content
➝ My sales personalized program
➝ My 1-on-1 Coaching Sessions
➝ My team Coaching Sessions

Now, how serious are you about building your Sales Career?

Let's make it happen.

👉🏼 Shoot me a DM, or head over to my Featured section.

I'll see you at the top!

Founder

Get smarter with Startup, Sales & SaaS news straight to your inbox.
A weekly email focused on the evolution of Startups, Sales, and SaaS. A fun and human voice. Everything you need to know in less than 5 minutes. No BS.

8 AI Prompts That Actually Book Meetings (Cold Email Advanced Edition)

(+ the exact wording I use to land 79+ meetings/month)

☑ ICP Research Prompt

“Act as a sales analyst. Analyse CTOs in B2B SaaS (100–500 employees). Summarise their top 5 priorities, daily pains, and buying triggers in less than 200 words.”

☑ Personalization Hook Prompt

“For this LinkedIn profile [link], draft 3 icebreakers. Keep under 20 words, avoid flattery, tie to their recent activity. Avoid jargon, buzzwords or being salesy.”

☑ Problem Hypothesis Prompt

 “Write 3 pain-point hypotheses for VPs of Sales in SaaS who missed quota last quarter. Keep each under 15 words. Make them relevant and give me a 1 line “Why it matters” for me to understand your POV”

☑ Objection Handler Prompt

 “Give me 3 tactical responses to ‘too expensive’ objection for SaaS buyers in X industry for Y role/title that are willing to buy [my solution]. Make it consultative, not defensive. Each reply must be under 25 words.”

☑ CTA Prompt

"Generate 3 high-converting CTAs for a SaaS demo request email. Each CTA must be under 12 words, avoid pushy sales language, and emphasize clear, outcome-driven value that motivates action without pressure. Prioritize clarity, psychological pull, and alignment with a business decision-maker mindset."

☑ Follow-up Prompt

"Craft a compelling two-sentence follow-up email for a prospect who opened but did not reply to my initial message [insert message 1]. Provide fresh value by weaving in a single new, research-backed insight or market trend that sparks curiosity and relevance, while keeping the tone consultative rather than transactional."

☑ Case Study Builder Prompt

"Transform the following customer testimonial into a concise, two-line cold email case study. Highlight quantifiable ROI, specific numbers, and credible impact in a way that feels authoritative yet humble—avoiding overt self-promotion while ensuring the results command attention and trust."

☑ Multi-Thread Prompt

"Identify 3 alternative stakeholders to approach if a VP of Sales does not respond. For each contact, justify their relevance by explaining their role in the decision-making ecosystem, their potential influence on the buying process, and how they could shape or accelerate a purchasing conversation."

♻️ Repost this so more people stop using GPT like an intern

This AI SDR outperforms 99% of SDRs.
He booked me in 2:06 minutes.
Full story:

I filled out a demo form, expecting the usual SDR dance.

Instead, Alex (Alta | AI Revenue Workforce's AI SDR) qualified me live and dropped a meeting straight into my calendar.

No delay.
No “let me check availability.”
No missed questions.

Just one clean, intelligent handoff.

And that’s when it clicked: This is going to replace your entire inbound flow.

No more reps scrambling to follow up.
No more leads sitting in HubSpot for hours.
No more meetings lost to slow response times.

Now reps get what they actually want: booked meetings.

Here’s what an actual AI Sales Agent should do:

→ Qualify in real time based on fit, urgency, and timeline
→ Book meetings instantly without rep lag
→ Route to the right AE
→ Learn and improve every conversation
→ Run 24/7, without fatigue or fallback

We rolled this out for a client:

• Speed-to-lead dropped from 1 day to 3 minutes
• +61% of qualified leads booked in under 5 minutes
• Pipeline built itself — faster and cleaner

This isn’t just automation.
It’s intelligence in motion.
It's Alta | AI Revenue Workforce

Don't believe me? Try it yoursel now: https://lnkd.in/dwBuHm9A

Brand partnership • CEOs: Broken pipeline & poor performer sales reps? I fix both for you in <60 days. You’ll hate how fast it works. | Modern Seller Program Founder

17.691.288 emails, 6.882.916 calls, and 15 years later, I realized something:

Sales isn’t hard because of objections.
It’s hard because of the emotional tax.

The giving.
The waiting.
The ghosting.

You don’t last by getting tougher.
You last by getting better at rebuilding.

EVERY. SINGLE. DAY

For you, my dear sales colleague:

You’ll survive Q1 and become stronger.

Agreed?

This is my inspirational post.

👉 Follow Alan Ruchtein for Modern Sales Frameworks.

“I used a tool to get your number. Want a demo?”
That was my opener on a cold call to a CEO last week.
First thing out of his mouth: 

“Who gave you my number?”

Most reps would never say that.
Too risky. Too blunt. Too honest.

Old-school playbook says:

- "Found it in my notes…"
- "We met at an event, maybe?"
- "Uh, your colleague passed it over."

I said:  “FullEnrich did. Your reps should use it too.”

He laughed.

Boom, we’re in.

No lies. No fake intros. No fluff.

The most dangerous thing in sales today? Playing it safe.

Safe = Ignored.
Safe = Generic.
Safe = “Thanks, not interested.”

Radical honesty cuts through faster than any script ever will.

Tools like FullEnrich get you access.
Truth gets you respect.

What's your #1 opener for cold calls?

My go-to 6 live frameworks for follow-ups. They work across email, LinkedIn DMs, and live calls to clearly recap and move conversations forward:

Most follow-ups fail because they try to “check in” instead of forcing a decision.

“Just checking in.”
“Any updates?.”
“Bumping this.”

Those don’t move deals forward.
They remind buyers you want something.

Strong follow-ups do the opposite:

→ restore clarity
→ re-anchor priorities
→ reduce decision friction

1️⃣ Clarity Recap

Re-align the conversation and confirm understanding.

Example: “To make sure we’re aligned here’s what I understood you’re aiming for [short description]. Did I capture that right?”

2️⃣ Silent Objection Check-In

Creates space for what hasn’t been said.

Example: ”Is anything on your side holding this up or something popped up internally I should be aware of?”

3️⃣ Priority Alignment

Refocuses on what matters most right now.

Example: “When we last spoke, {{priority}} was top of the list. Is that still the case, or has anything shifted?”

4️⃣ Micro-Value Nudge

Moves the conversation forward naturally.

Example:“Sharing a quick resource that other teams found useful when tackling [X], thought it might be helpful for you too.”

5️⃣ Time-Pressure Mirror

Reflects their timeline without pushing yours.

Example: “Are you still hoping to get this sorted before {{timeline}}. If so, you shoul act by doing X before Y. May I help there?”

6️⃣ Decision Simplifier

Reduces friction by making the next step easy.

Example: “If it helps, I can put together a simple 1-page summary so you can review the key points?”

Good follow-ups don’t chase.

They guide the next step.

I might be able to help you avoid all the ghosting you’ll get in Q1 and hit quota faster by working together using my proven methodology.

If you want that to happen, DM me “ELITE” and let’s make you unstoppable.

Or take action by getting The Modern Seller Program “Q1 Zero Excuses Limited Offer” like other +1129 heroes did at 60% OFF. Last 48 hours: 

https://lnkd.in/dR_CRPGc

👉 Follow Alan Ruchtein for sales frameworks & AI playbooks that actually close.

The 5 solutions I wish I’d had when I started my sales career 15+ years ago (that help me consistently book 70+ meetings/month)

1 — FullEnrich

Your outbound dies the moment your data is wrong. FullEnrich fixes that before your reps even touch a lead.

→ Cleans & verifies every contact
→ Confirms emails & phone numbers
→ Removes dead records instantly

2 — Perplexity

Real-time intelligence while you browse a prospect’s world.

→ Scans sites, posts, PR, product pages
→ Surfaces buying triggers + priorities
→ Generates POVs instantly

3 — RetroFix (YC S24)  

Call prep that feels like cheating.

→ Auto-scans your calendar
→ Builds insight briefs for each meeting
→ Delivers pains, angles, talk tracks

4 — Alta | AI Revenue Workforce  

Outbound that reacts the moment intent spikes.

→ Outbound agent triggers personalized messages
→ Inbound agent qualifies warm leads instantly
→ Both adjust messaging based on behavior

5 — Instantly.ai

High-personalization at scale without burning domains.

→ Behavior-based sequences
→ Smart send logic
→ Maintains deliverability

If you want more AI-native outbound systems follow Alan Ruchtein, the playbooks only get sharper from here.

New year. New format. Same obsession: Telling the truth about sales:

For the last couple of years, sales content has been everywhere.

Posts. Threads. Frameworks. Hot takes.

Useful? Sometimes.
Human? Rarely.

But sales isn’t just read. It’s felt.

Tone matters.
Pace matters.
Timing matters.

You remember a voice long after you forget a post.

People don’t trust content.
People trust people behind content.

𝗧𝗵𝗮𝘁’𝘀 𝘄𝗵𝘆 𝗖𝗼𝗻𝗳𝗲𝘀𝘀𝗶𝗼𝗻𝘀 𝗼𝗳 𝗮 𝗦𝗲𝗹𝗹𝗲𝗿 𝗶𝘀 𝗰𝗼𝗺𝗶𝗻𝗴 𝘁𝗼 𝗹𝗶𝗳𝗲.

Together with Kevin, we’re creating a podcast that talks sales the way you actually experience it. 

- The pressure 
- The uncomfortable calls
- The wins that almost fell apart 
- The tools you can use now to win deals.
- The moments nobody turns into a carousel.
- The way you can shape your mindset to win.

And this time, it’s not staying in text.

This year, we’re putting all of this and more over YouTube and TikTok, where tone, pauses, and reactions say more than words ever could.

No polished performances.
No sales theater.

Just real conversations about what it actually takes to win in sales today.

We have 2 final sponsor spots open for brands that want to be associated with honest, high-trust, and insanely tactical sales content.

DM Kevin or me directly if that’s you. Don't cry later!

Stay tuned, more news coming soon...

PS: Link with details in the comments.

This simple 6-step process tweak in my prospecting routine changed everything:

01 — Spot Accounts Showing Real Movement

Pipeline grows when outreach starts with signs of activity.

Look for:

→ VP/CRO job changes
→ Hiring sprints
→ Funding events
→ Tech stack swaps

AI Prompt: “Analyze this account and list 3 buying signals with explanations of what each signal means for pipeline, urgency, and timing.”

02 — Turn Signals Into a POV That Actually Lands

A buying signal only matters when it’s connected to urgency. A strong POV answers:

1️⃣ What changed
2️⃣ Why it matters
3️⃣ How it impacts pipeline, revenue, or efficiency

AI Prompt: “Turn this buying signal into a sharp POV for a VP of Sales. Keep it under 40 words and link it to pipeline quality.”

03 — Build Relevance in Under 20 Seconds

Fast relevance lowers resistance.

AI pulls instant context from:

✓ LinkedIn
✓ Website
✓ Hiring trends
✓ Tech stack

AI Prompt: “Summarize this prospect’s last 5 actions (posts, hires, tech changes) and turn it into a 20-second personalized intro.”

04 — Trigger Outreach Based on Behavior

Modern outbound reacts to intent — not timers.

If they:

✓ Click → send an insight
✓ Open → send a POV
✓ Watch → send a case study
✓ Ignore → change the angle

AI Prompt: “Based on this behavior event (open, click, watch), recommend the next message that would create maximum relevance.”

05 — Align Messaging to Real Pain

Personas describe audiences.
Signals describe realities.

Replace: “Head of Sales at SaaS companies” with “Teams missing pipeline coverage because SDR productivity dropped 27% in Q3.”

AI Prompt: “Translate this ICP persona into 3 real pains backed by buying signals, not assumptions.”

06 — Automate What’s Proven to Work

Your best talk tracks shouldn’t disappear after a good call.

Turn wins into:
✓ Scripts
✓ Prompts
✓ Templates
✓ Micro-frameworks

AI Prompt: “Analyze these 5 won-deal calls and extract:

– patterns that created trust
– language that moved the deal forward
– objections that repeated
– winning talk tracks to templatize.”

If this feels like what your team is missing, follow Alan Ruchtein for real fixes

Here’s the truth no one tells you about AI AGENTS in 2026 and you must know before it’s too late:

Most teams talk about “AI SDRs” like it’s some futuristic thing.

It’s not. 

It’s just the new way top outbound teams already operate in 2026.

If you want an AI SDR that actually books meetings and not just another bot sending spam, follow the exact blueprint I use with my clients 👇

1️⃣ Map the SDR workflow

Before you automate anything, break the job into small stuff

This includes researching accounts, spotting triggers, writing emails, personalizing, qualifying inbound, following up, and updating the CRM.

 If you don’t know what the AI should own, nothing will work.

2️⃣ Assign each responsibility to its own AI agent

Think of it like building a tiny GTM team:

• CRM Agent
• Inbox Agent
• Writer Agent
• Trigger Agent
• Research Agent
• Sequencer Agent

 Each one handles a specific part of the process so nothing gets dropped.

3️⃣ Train the AI to think like your best SDR

Give it a persona, feed it your ICP pains, your POVs, your proof.

Let it write the emails, the call scripts, the follow-ups, the objection handling.
Save your best prompts somewhere and reuse them. Don't start from scratch every time.

4️⃣ Turn the whole thing on

A signal fires, research happens instantly, a fresh POV gets created, the message goes out, follow-ups happen automatically, CRM gets updated, and managers get notified when something matters.

No lag. No guessing. No “I forgot.”

5️⃣ Track everything and refine it

Open rate, reply rate, positive replies, meetings booked, time-to-first-touch.

Every cycle makes the system smarter.
 
Modern AI AGENTS don’t replace reps.

They replace everything that slows reps down.

Follow Alan Ruchtein for more AI-native outbound playbooks and the exact workflows that will separate the leaders from everyone else in 2026

I trained GPT on 1000s of real sales calls and emails. Now it sells on my behalf. STEAL the 30 prompts every modern rep needs below (FOR FREE):

They include topics like:

→ Detect missed discovery signals

→ Turn messy notes into CFO memos

→ Even simulate a skeptical CEO objection

→ Draft Core vs Premium proposals in seconds

→ Write ROI-based pricing breakdowns automatically

And 25 more…

And I’m giving the full list away.

Want it?

1️⃣ Like this post
2️⃣ Comment “GPT”
3️⃣ Make sure we’re connected so I can DM it to you

(P.S. You’ll never look at your CRM or deal reviews the same again.)

My go-to 20 highly relevant signals for consistent +7% reply rates in my outbound campaigns:

Buyers rarely tell you when they’re ready

They drop signals way before you notice.

But top sellers spot the subtle signals that quietly say:  “This company is getting ready to buy.”

They are:

1) New Funding Round
2) Key Leadership Hire
3) Sudden Team Layoffs
4) Rapid Hiring Spikes
5) New GTM Leader
6) Product Launch
7) Tech Stack Swap
8) Pricing Changes
9) Competitor Move
10) High-Churn Reviews
11) Website Redesign
12) Hiring for Pain Keywords
13) Industry Regulation Change
14) New Market Expansion
15) New Partnership
16) Negative Press
17) Flat Quarter or Revenue Drop
18) Big Customer Win
19) Founder or CEO Publicly Posting About Pain
20) Job Postings with “Fix” Language

👉 Follow Alan Ruchtein for elite outbound, GTM strategy, and AI-driven sales frameworks that actually close deals.

Or better, DM me so I train you personally and your team on how to be a Modern Seller in 2026 without getting a burnout.

PS: Last 24 hours to get The Modern Seller Program “Q1 Zero Excuses Limited Offer” like +1129 heroes did at 60% OFF: https://lnkd.in/dR_CRPGc

One of my clients burned $80k before realizing step 1 was wrong:

They were a fast-growing B2B SaaS team.
Just raised a round.
Ready to scale outbound.

So they did what most execs do:

→ Hired 3 reps
→ Bought lead lists
→ Wrote solid copy
→ Hit send

And waited.

The results?

- 18% open rates
- 0 meetings booked
- Reps blaming the messaging
- Founders blaming the reps

They even considered scrapping outbound altogether.

But the problem wasn’t the team.
It wasn’t the message either.

It was infrastructure.

No one checked the sending setup.
No one tracked reputation.
No one built a real system to protect their inboxes.

They were firing campaigns from burner Gmail accounts and wondering why nothing landed.

That’s when we brought in Maildoso.

Here’s what changed:

✅ Self-healing mailboxes
✅ Google Workspace + SMTP rotation
✅ US-based IPs, real domains
✅ Deliverability monitoring + auto-replacement

Fast forward 30 days:

- 98%+ inbox placement
- 5 meetings/week
- Cold email went from a gamble to a pipeline engine

Lesson?

Step 1 of outbound is NOT copy.
It’s not hiring reps.
It’s not even building lists.

Step 1 is infrastructure.

No infra = no delivery
No delivery = no pipeline
No pipeline = no growth

Cold email isn’t broken.

Most companies just skip the foundation.

Don’t be that guy. Do outbound properly.

Inbox or nothing.

PS: Guess where I was in that picture, and I’ll send you my AI GPT cold email bot for FREE in your DMs.

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The Battle

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