🤖 ChatGPT upgrade

In partnership with

To access all my premium resources, please upgrade to Premium

AI is changing sales. Are your emails keeping up?

You’re already using ChatGPT to draft smarter outreach.

Now imagine combining that with a platform built to send, personalize, and scale those emails automatically.

That’s where lemlist comes in.

✅ AI-ready: plug your ChatGPT prompts straight into multi-step sequences
✅ Personalization that stands out (images, videos, dynamic text)
✅ Deliverability engine to keep AI-written emails out of spam
✅ Multi-channel workflows (email + LinkedIn)
✅ Real-time tracking & analytics

Thousands of SDRs and founders are pairing ChatGPT with lemlist to book more meetings with less manual work.

⇒ Try lemlist and put your AI outreach on autopilot

How AI-powered context delivers better outputs

Ryan Staley breaks down how elite GTM teams usually reach top-1% results by applying systems to effective AI workflows, not simply chasing your new “advanced tools” instead:

Context and memory usage

➔ Provide AI with company details, and specific instructions once.

➔ This becomes an ongoing “brief” so outputs are made tailored.

➤ Example: A sales manager calibrates for ICP details and target accounts. Each pipeline review or call preps displayed feel custom without additional re-explaining.

➤ For neutral outputs, utilize your responses to ignore memory.

Keep resource catalogues

Keep a library of resources when value-adding prompts.

✔ Great lead qualification scoring

✔ Risk messages from usage data

✔ Pipeline reviews with health flags

✔ Competition behind public filings

Repeatable AI frameworks

❖ Don’t settle for just one broad question.

❖ Move macro → micro with frameworks like SPICED, MEDDIC, or AIDA.

Example: Ask for SPICED discovery frameworks, then highlight “pain points” prompt automation by expanding with tailored discovery questions for your next call.

World-class private consult

Prompt AI to become an expert and model their perspective.

➤ Elon Musk → First principles thinking approach

➤ Steve Jobs → Persuasive storytelling for exec presentations

➤ Warren Buffett → Potential risk vs. ROI investment framing

➤ Sam Altman → Descriptive product roadmap critiques

One CRO saved almost weeks by using “Steve Jobs” consult to design board decks.

Your “10x better” techniques

After getting response, push AI to “make it 10x better.”

✱ Example: An SDR drafts an opener email, then repeats until his outputs are sharper, and more relevant than his original response drafts.

✱ Example: Revise a proposal summary by making everything “10x better” until things are being read like an effective CFO-ready business case.

Systematize your moves and become one true GTM partner.

AI personalization that every salesperson needs

Sam Knight outlines four effective AI business tools every sales rep should begin using to quickly touch-up researches, improve customer outreach, and build stronger pitches:

Grok for quick research

Most reps panic before calls, Googling for company details.

➤ Before a call, ask for a revenue snapshot of your target account

➤ Question for company size, growth stages, or leadership moves

Grok pulls revenue, funding, headcount, even insights from X.

ChatGPT for manual work

Establish your ChatGPT “full-cycle SDR” sales agent model.

✔ Research 20 prospects and generate personal messages

✔ Build icebreakers tied with recent news, events, or funding

✔ Automate repetitive SDR tasks and focus more on closing

Agents select the best sources, and higher-quality output.

Manis for presentations

Weak presentations are costing you secured deals.

❖ Personalize slides with your customer’s objectives

❖ Generate refined, and credible presentation decks

❖ Build your own Instagram-style visuals if needed

Manis builds professional decks from a simple outline.

Clay AI for enrichments

Clay automates manual searching through databases.

⇢ Enrich leads with funding, revenue, hiring, and recent news

⇢ Pull direct contact info by adding straight into your CRM flow

⇢ Gather real-time alerts on buying signals when timing’s right

FREE ChatGPT Resources

Don’t lose prospects to reps who sounds like they've known your leads for years. These ChatGPT prompts delivers your unfair advantage of transforming cold outreach into warm conversations feeling like you’ve always known their problems and goals.

Your competition's send generic templates, while you personalize messages at scale. Download this FREE ChatGPT Prospecting resource and start booking meetings like you have insider: because your outreach feels like you've known their business for months.

Download the FREE ChatGPT sales resource now!

Handle objections effectively with AI prompts

Haris Halkic provides how to use ChatGPT to make your discovery calls, and objection handling sharper by getting you to sound credible, uncover pain quicker, and close better:

✔ Discovery call decoder

Ask: “Based on this company description: {paste}, give me 5 discovery questions tailored to a {job title} at a {company type}.”

➔ Example: Paste the website of a fintech startup.

✔ Objection anticipator

Prompt: “I’m selling {product} to {persona}. What are the 3 most likely objections I’ll hear? How should I respond with confidence and value?”

➔ Example: Selling HR software to a VP of People.

✔ Call opener generator

Prompt: “Write a 60-second intro for a discovery call with a {job title}.”

➔ Examples for a CFO: “I won’t take much time. Curious how you’re thinking about rising SaaS costs this quarter?”

This opener feels low-pressure, not scripted.

✔ Instant deal killer signal

Feed LinkedIn text or a company website.

Ask: “What signs suggest they’re a bad fit or time-waster?”

➔ Example: ChatGPT flags recent downsizing, suggesting budget may be frozen.

✔ Competitor contrasts

Prompt: “Our biggest competitor is {name}. Give me 3 clear, honest ways we’re different.”

➔ Example against Salesforce: “We’re lighter to implement, simpler to customize, and designed for mid-market teams with no admin overhead.”

✔ ROI discussion point

Prompt: “Provide me 3 business outcomes connected with {product} when speaking with a {seniority level} buyer.”

➔ Example for a CRO: “Reduce customer churn by 15%” → “Shorten deal cycles by 20%” → “Add $3M in upsell pipeline.”

✔ Persona cheat sheets

Ask: “Create a snapshot of {job title} at a {company type}. What are their goals, metrics, and frustrations?”

➔ Example: For a Head of RevOps at a SaaS company: Goals = pipeline accuracy

Metrics = forecast accuracy %; Frustrations = dirty CRM data, manual reporting.

✔ Demo prepared lines

Prompt: “I’m about to show {product} to a skeptical buyer. Write a 2-line intro that frames the demo around their goals.”

➔ Example: “You mentioned renewals slipping last quarter. Let’s focus on how this workflow helps your team spot churn risk earlier.”

✔ Story-based evidence

Ask: “Give me a short customer story about {pain point} solved by {product}.”

➔ Example: “A mid-sized bank cut loan approval times from 10 days to 2 using our platform. Their COO told us it was the first time tech actually sped things up for compliance.”

✔ Rep sales confidence

Prompt: “Act as a skeptical {job title} and role-play a discovery call with me. Ask tough questions.”

➔ Example: ChatGPT fires: “Why should we pay for this when my team already built something internally?” ➔ Practice responding under pressure.

Look prepared by handling meetings with great confidence.

Partnering with these newsletters:

• The Follow Up: We talk about Sales like your friend, not your manager

• Big Desk Energy: Startup stories and lessons

• B2B Whales: Proven B2B sales strategies

• Creator Spotlight: Grow with social media and newsletters

Check them out!

P.S. Get access to all my premium resources and infographics - subscribe to Premium