🤖 tired of generic AI results?

Targeted outreach using specific ChatGPT process

I just added a brand-new chapter to AI Sales Mastery. It’s super useful for anyone using ChatGPT, Perplexity, or similar tools for sales research.

My take on ChatGPT & Co.:

These tools aren’t “true” artificial intelligence. They’re more like super-powerful computers.

And computers only produce great output if you give them precise instructions and the right data to work with.

Most salespeople make the same mistake:

They throw vague prompts at AI and get generic, half-useful answers. Then they wonder why it’s not helping them win deals.

In this new chapter, I walk you through a process for:

• Pulling real, verifiable insights from any company

• Avoiding AI’s tendency to guess and assume

• Turning that intel into highly targeted cold emails and call prep

• Scaling the process with automation or VAs

If you want AI to give you account-specific intel you can bet your quota on, this is how you do it.

You’ll see exactly how I used this to uncover churn problems, enterprise gaps, and pricing pushback at a target account - insights generic prompts would never surface.

The chapter’s live now inside AI Sales Mastery.

⇒ Get ahead before AI becomes the norm

Prepare like strategists using AI in minutes

Matt Green outlines prompt sequences for account research that eliminates shallow discovery and builds instant credibility. Ask prospects valuable, result-focused questions:

Prompt 1: Setting your context

"I'm an account manager for [your company]. My target account is [prospect company]. What are their top 5 business challenges for 2025–2027?"

➤ This gets you forward-looking, and company-specific, not just generic issues

Prompt 2: Map issues to people

"If this is true, who are the key decision makers in each of those respective areas?"

➤ You’re now linking each challenge to higher authority with budget and power

Prompt 3: Go deep on executives

"My best option is pursuing [executive name]. Can you identify their organization and give me insights on how to engage them?"

➤ You get org structure and working view of that person’s goals and pain points

Prompt 4: Build multithread map

"Provide me two on-the-line and two below-the-line contacts in this executive's organization and why they're important."

➤ Power map = done. This builds you with contact strategy across multiple levels

Prompt 5: Writing hook openers

"Based on their strategic priorities, what's the most compelling business case for [executive] to take a meeting with someone from [your company]?"

➤ Not features, just valuable props made around the desired business outcomes

Minimize hours of research using prompts

Alex Berman breaks down quick, and repeatable AI-driven prompts helping uncover buyer challenges in minutes, using nothing but LinkedIn profiles and company websites:

ChatGPT to find buyer problems

Most reps waste hours doing manual research for cold emails and still miss the mark.

Use AI to generate realistic “confession-style” posts from their unfiltered point of view.

➤ Begin with Sales Navigator

Filter by position title, company size, and location to find relevant leads.

➤ Looking for primary inputs

Copy their LinkedIn headline, work history, and company website texts.

➤ Use this prompt in ChatGPT:

“Write a Reddit post from this person’s point of view where they admit everything is going wrong at work. No sugarcoating.”

❖ Forces AI to surface pain points depending on business context

❖ You’re looking for business problems worth testing in outreach

Turn pain into sharp messaging

Once you get the results, highlight 3–5 pain points.

Ask ChatGPT to build cold pitch angles around them:

Prompt:

“Highlight 5 pain points in their words and how to use them to pitch outbound/email/lead gen.”

Example output:

✱ “Revenue has plateaued”

↳ Inject refreshingly new outbound pipelines

✱ “Marketing is burned out” 

↳ Free up internal teams with external capacity

✱ “Tired of pretending whitepaper downloads are wins”

↳ Emphasize conversations, not vanity metrics

You don’t need to use all of them, pick something real and test it.

Run process for other industries

This works for any persona:

✔ Selling group insurance? Look for HR executives

⇒ Common pains: Turnovee, DEI burnout, injury report problems

✔ Selling MarTech? Look for CMOs or marketing VPs

⇒ Common pains: Innovation fatigue, surface-level campaigns

✔ Selling SaaS to enterprise? Use headcount filters

⇒ Use company news and website copy for better information

Don’t take AI-produced output at face value.

Just rerun tests or tweak prompt when needed:

“Include pain points that would trigger an insurance liability issue”

AI Research ≠ AI Writing Voice

Alex makes this clear:

✘ Don’t let AI write cold email messages

✘ Generic ChatGPT sends won’t convert

✔ Only use AI for research and ideation generation

✔ You still need choose voices to write like humans

Know when AI override is needed

AI guesses. Sometimes it fabricates. Don’t blindly trust.

❖ Validate the ideas with your personal judgment

❖ If outcome is substandard, challenge and rerun

❖ Use results to spark your thinking, not replace it

Example AI prompts that work

1. “Write a Reddit post from their POV admitting their business is currently messy”

2. “Highlight 5 pain points from this and how to pitch [insert offer] to prospects”

3. “Regenerate ideas with a focus on [compliance issues / burnout / sales pipeline]”

Bring value or get replaced with urgency

John Barrows explains why the sales process isn’t really dying but irrelevant, unprepared reps are slowly vanishing. Sell your product before prospects even reveal themselves:

Step 1: Topic discovery

Prompt:

“I’m a B2B sales rep trying to create a high-value 2–3 page briefing doc. What are 5 non-obvious, insight-rich topics that would be helpful to a [job title] in [industry]?”

➤ This gives you unique angles that go beyond surface-level fluff

Step 2: Deep immersion

Prompt:

“Get topic #3 and build a 2–3 page white paper. Include recent data, trend analysis, real examples, and clear takeaways in business-relevant language.”

➤ Walk into dials with content that makes your buyers smarter

What buyers now want from reps

Prospects don’t need you to “walk them” what they already know.

Your potential customers want you to:

→ Make them smarter with knowledge

→ Portray what they have been missing

→ Help them make better decision faster

If you’re just regurgitating info they already know, you’re obsolete.

If you can teach something they didn’t know? You’re indispensable.

Partnering with these newsletters:

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• B2B Whales: Proven B2B sales strategies

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Check them out!