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Master Challenger Sales and MEDDIC qualification with ChatGPT. Learn to research smarter, engage stronger, and close faster with Koshima’s AI sales programme.

Sales Leaders & Account Teams: Challenger Sales with ChatGPT

Smarter, Stronger Selling.


Overview

In today’s B2B sales environment, customers have done their homework. They arrive informed, cautious, and ready to challenge your value. To stay ahead, sales professionals need to move beyond traditional relationship selling and start leading conversations with insight.

Challenger Sales with ChatGPT is a four-part interactive enablement series designed specifically for sales leaders, account managers, and business development professionals. It combines the proven Challenger Sales methodology and MEDDIC qualification framework with the practical use of ChatGPT, teaching participants how to use AI as a sales intelligence partner.

You’ll learn to research smarter, engage more meaningfully, and qualify more effectively using generative AI.


What You’ll Learn

1. Research Customers Smarter

Uncover deep customer insights in minutes. Learn how to use ChatGPT to:

  • Analyse your prospect’s business model, industry landscape and challenges.
  • Conduct whitespace analysis and identify growth opportunities.
  • Build data-grounded hypotheses that set up impactful Challenger Style conversations.

2. Customer Insight & Messaging

Turn intelligence into influence. We’ll guide you through:

  • Crafting tailored outreach that teaches customers something new about their world.
  • Using ChatGPT to create customer-specific messaging and value propositions.
  • Framing conversations that shift perception and establish credibility.

3. Opportunity Qualification (MEDDIC)

Structure your pipeline with precision using the MEDDIC framework. Learn how to:

  • Identify measurable customer metrics and economic buyers.
  • Clarify decision processes and success criteria.
  • Build your internal champions using ChatGPT to map influence networks and stakeholder language.

4. Engagement Strategy & Closing

Bring it all together with disciplined execution. You’ll learn how to:

  • Develop engagement plans that align Challenger insights with customer priorities.
  • Use ChatGPT to anticipate objections, prepare for negotiations, and refine proposals.
  • Close deals faster by focusing on the right opportunities, with confidence and clarity.


Workshop Structure

Duration: 4 x 2-hour live sessions

Delivery: Online via Microsoft Teams

Dates: Thursdays, 5–7 PM GST

  • 27 November – Research Customers Smarter
  • 4 December – Customer Insight & Messaging
  • 11 December – Opportunity Qualification (MEDDIC)
  • 18 December – Engagement Strategy & Closing

Group Size: Limited to 12 participants

Includes: Post-workshop learning kit and prompt templates


Outcomes

By the end of the series, participants will be able to:

  • Conduct customer and market research using AI tools like ChatGPT.
  • Build Challenger-style insight-led sales approaches.
  • Apply the MEDDIC framework to qualify and govern opportunities.
  • Craft AI-assisted engagement and follow-up strategies.
  • Drive pipeline efficiency and increase win rates through smarter preparation and focus.


Cost

AED 1,139 per participant

Includes:

  • 4 x 2-hour live interactive sessions
  • Guided exercises using real sales scenarios
  • Custom ChatGPT prompt library for sales
  • Certificate of completion 


Course Director

Carlo Pepe

AI Business Consultant with 25+ years in sales and consulting. Formerly with Singapore Telecom, Rackspace and Dell Technologies, Carlo specialises in helping organisations apply AI practically, enabling sales teams to sell smarter, faster, and with measurable results.


Ready to Sell Smarter?

Secure your seat now and transform how your team researches, engages, and wins with AI.

Spaces are limited. Terms & conditions apply

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