🤖 ChatGPT toolkit

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Stress-test positioning before official launch

Maja Voje discusses how AI supercharges your GTM execution. Utilize structured prompts delivering ICP sales clarity, actionable strategies, with effective messaging:

Customer pain discovery

❖ Understanding pain is the foundation of effective GTM.

Ask: “Summarize top 3–5 pain points faced by [ICP] when evaluating or using solutions in [product category]. Include emotional drivers, business impact, and current workarounds.”

❖ Helps reveal frustrations and how they’re giving solutions.

Buy trigger identification

↳ Knowing what makes buyers start looking is necessary.

Ask: “What events or situations push [ICP] to look for [product]? List the most common internal and external triggers with urgency levels.”

↳ Establishes when to reach out during perfect moments.

Objection-handling prep

✱ Objections stop deals cold when you’re not anticipating.

✱ AI workflows helps prepare for these kind of scenarios.

Ask: “List primary objections a [job title] would raise when evaluating [product type]. Include various budget, technical, and political blockers.”

✱ Arms you with responses disarming prospect’s hesitation.

ICP customized building

➤ You need accurate ICPs with context for decision-making.

Ask: “Build 3 ICPs for [product]. Include applicable company type, size, industry, buyer roles, primary goals, and decision-making context.”

➤ Produces actionable ICPs that guides pipeline outreach.

Positioning risk checklist

✔ GTM strategies fail because of inconsistent messaging.

Ask: “What are common GTM positioning mistakes in [industry]? Depending on the ICP and specific product, what potential traps should we avoid?”

✔ Keeps your narrative crisp to avoid messaging errors.

Feature-to-benefit relation

❖ Product features are rarely sold.

❖ Benefits tied with outcomes do.

Ask: “Translate feature lists into benefits that matter to [ICP]. Show transformations beginning from feature → outcome.”

❖ Example: “Automated workflows” becomes “Cut onboarding time by 40%.”

Simplified messaging tests

➔ Complex explanations turn buyers off.

➔ Explain the product’s impact directly.

Ask: “Explain our product to a [job title] with no technical background in under 100 words. Jargon-free, focused on impact.”

➔ Forces clarity so everyone discern value.

GTM technique mapping

✱ Choosing wrong GTM motion wastes time and resources.

Ask: “Based on our stage and ICP, what 3 GTM motions are viable (inbound, outbound, product-led)? Explain pros, cons, and team needs.”

✱ Aligns your team with motions fitting maturity and market.

Competitor GTM teardown

↳ You can’t differentiate without knowing competitor playbooks.

Ask: “Analyze the GTM strategy of 2–3 competitors. Focus on ICP targeting, positioning, pricing, content, and distribution. Show where we can differentiate.”

↳ Example: If competitors lean enterprise, own mid-market speed.

Growth cycle brainstorms

✔ Sustainability comes from loops, not just one-off campaigns.

Ask: “Suggest 3 growth loops we can test for [product]. Include user behavior driving said loop, various incentive, and scalability potential.”

✔ Example: Referrals, usage-based sharing, or adoption integrations.

Build repeatable simulation with AI prompts

Steve Cary breaks down how to use ChatGPT in voice mode to simulate mock sales calls with real-sounding conversations, helping practice difficult response scenarios anywhere:

How the AI mock sales call works:

• AI plays the customer role, while reps do the selling part.

• You feed the AI scenario prompts that clearly defines:

  ➔ The client background (e.g., skeptical CEO, detail-heavy lead)

  
  ➔ Kind of meetings conducted (second call, final negotiations)

  
  ➔ Common prospect objections mentioned likely by customers

Example Scenario 1:

Client: John Peterson, CEO of Peterson Enterprises

Background: Curious with AI workflows but skeptical

Objection: “We’ve done fine for 20 years without AI. Why change now?”

Practice answer: Explain AI’s compounding growth, competitor adoption, and why experimenting minimizes business’ long-term potential risks.

Example Scenario 2:

Client: Operations Director of a mid-sized manufacturer

Background: Concerned about ROI, resistant to new vendors

Objection: “I don’t have time for experiments. Show me actual proof of results.”

Practice answer: Provide customer success metrics, quick-win case study analysis, explains incremental pilots to demonstrate ROI growth quickly.

➤ Base Mock Sales Call Prompt

✱ Set up automation with client-facing role

✱ Loads objection and background context

✱ Process roleplays in voice mode options

➤ Scenario-Switching Prompt

❖ Lets you replace text inside with your own contexts

Example fields:

❖ Scenario: “Outsourced accounting services pitching on time-bounded CEO”

❖ Client background: “Impatient, wants ROI, skeptical of external vendors”

❖ Objections: “Too expensive,” “Already have in-house staff,” “Show me proof”

Expand your description into realistic scenarios creating objections for practice.

Other AI Usage Examples:

↳ Onboarding new reps: Create disscussion where new AE faces price objections

↳ Preparing for a demo: Simulate prospect who interrupts during conversations

↳ Upselling clients: Train with mock CFO who strongly resists AI process upgrade

↳ Tough closing call: Run scenarios where competitors undercut on value pricing

These situations can be AI programmed with just realistic descriptions.

FREE ChatGPT Resources

Stop losing your potential deals to equipped competitors. These ChatGPT prompts deliver unfair advantages of knowing exactly what prospects think, feel, and need before you even touch second base. Transform hours of research into minutes of goal precision.

Your competition’s still guessing, and you'll be knowing. Download this free infographic ChatGPT AI preparation resource now and start closing potential deals like an error-free mindreader: because with these AI prompts, you can just read everyone.

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Establish presence with customized outreach

Ian Koniak explains how to consistently book meetings using repeatable systems. Breaking through crowded environments requires different, unique sales approach:

Scrape narrow before going deep

❖ Don’t spray your whole patch in just one moment

❖ Pick 10–20 accounts transforming your sales cycle

Use various channels every time

If you rely on emails alone, you slowly get invisible.

➤ Send an email → call right after → leave voicemails → follow with LinkedIn note, personalized video, or customized voice message

➤ Automation dial tools make prospect calls easier

Following-up leads consequently

✱ Big deals secured rarely come from only 2 touch bases

✱ Ian’s largest wins needed 10–15 before even meeting

✱ Executives notice persistence backed with preparation

Hyper-personalize using AI tools

Avoid “Hope you’re doing well.” greetings.

Every message should feel personalized.

Structure:

✔ Line 1 → Personal compliment tied with research

✔ Line 2 → Observation according to personal goal

✔ Line 3 → Gap between today and future visions

✔ Line 4 → How to aid prospect close various gaps

✔ Close → Soft CTA for taking action on movement

ChatGPT-4o prompt that works

“I’m a sales rep at [Company] targeting [Name, Title]. Write a personalized, executive-ready email that speaks to their role, their publicly stated goals or quotes, and how we can help them. Be concise, use bullet points, and end with a soft CTA.”

This prompt gives messaging that feels authentic and credible.

Where these methods shine:

↳ When the account uses your product (reference instantly)

↳ When public info is limited (personalize the account level)

↳ When you need to arm internal champions using materials

Executives respond to persistence, and proof you’ve done the work.

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