AI Prompting and Automation: How-To Series

How-To Series

AI Prompting and Automation

Improve your AI prompting and automation, today's most in-demand B2B marketing skills, with this all-new, 4-part how-to series. Hosted by PRO-favorite marketing experts Andy Crestodina and Christopher S. Penn.

Andy Crestodina and Christopher S. Penn

September 3, 10, 17, 24

12:00pm ET | 9:00am PT

Each session is 60 minutes

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Series Overview

B2B marketers are adopting AI tools for everything from content creation to research, automation to analytics, and more.

And to get the most effective results from AI, you have to go beyond basic prompting with ChatGPT, Gemini, and Claude.

Discover how today's best AI marketers use gen AI in B2B marketing. In this 4-part how-to series, hosts Christopher S. Penn and Andy Crestodina go deep into the techniques that'll make your AI prompts more effective and efficient.

This how-to series requires a ChatGPT Plus, Claude PRO, or Gemini PRO account—your choice. As of August 1, 2025, each is $20 per month. Higher-tier, team, and enterprise accounts will work, too.

Sessions

Session 1

AI 101: Marketing AI Prompting Basics

September 3

12:00pm ET | 9:00am PT

60 minutes


Anyone can write a prompt. But getting great results from AI is a skill. In this session, Andy shows you how to develop your skills to create powerful, reusable prompts that yield superior results.

In session 1, you'll use AI to:

  • Design high-performing prompts around a timeless framework
  • Draft, test, and revise reusable prompts and store them in a prompt library
  • Train the AI on your target audience

Better inputs mean better responses. And as the human behind the prompts, you'll scrutinize results, test prompts, and revise your work for ever better performance.

This how-to series requires a ChatGPT Plus, Claude PRO, or Gemini PRO account—your choice. As of August 1, 2025, each is $20 per month. Higher-tier, team, and enterprise accounts will work, too.

Session 2

7 Categories for AI Use Cases

September 10

12:00pm ET | 9:00am PT

60 minutes


You're already using AI to generate and repurpose content. But are you using it to find and target ideal customers, gather prospect data from LinkedIn, or build a marketing plan? In this session, Christopher S. Penn reveals seven B2B use cases made possible with beyond-the-basics AI techniques.

In session 2, you'll use AI to:

  • Build an ideal customer profile (ICP) based on existing data, score new leads against that ICP, and adjust your sales pitch based on that lead score
  • Generate new data from existing data to build a B2B marketing strategy targeting ideal clients
  • Summarize big data sets for sales team management and assessment using NotebookLM

With seven different use cases focused on B2B marketing, you'll find new ways to target your ideal clients and evolve your marketing and sales teams' performance.

This how-to series requires a ChatGPT Plus, Claude PRO, or Gemini PRO account—your choice. As of August 1, 2025, each is $20 per month. Higher-tier, team, and enterprise accounts will work, too.

Session 3

AI for Every Funnel Stage: From Content to Conversions

September 17

12:00pm ET | 9:00am PT

60 minutes


Andy reveals how AI can optimize your funnel, from inbound content to lead nurturing. You'll find gaps you hadn't noticed before, and measure your campaign performance for AI-powered insights.

In session 3, you'll use AI to:

  • Discover the topics that drive engagement and brand mentions
  • Turn ideas into outlines and outlines into drafts
  • Spot gaps on your key pages where business leads are born
  • Upload reports to your favorite LLM for quick marketing insights

Each of the methods is practical. But the real value is in the concepts, how they demonstrate the capabilities of AI, and how they can trigger your imagination.

This how-to series requires a ChatGPT Plus, Claude PRO, or Gemini PRO account—your choice. As of August 1, 2025, each is $20 per month. Higher-tier, team, and enterprise accounts will work, too.

Session 4

Combining Prompting Into Automations

September 24

12:00pm ET | 9:00am PT

60 minutes


Let AI automate your marketing tasks and take actions on your behalf. Chris will show you how to put your new prompting skills to use by building automations for effective, mostly-hands-off marketing.

In session 4, you'll use AI to:

  • Choose social media metrics based on different business goals such as brand building, lead generation, or community engagement
  • Walk through social media analytics tools—both native platform analytics and third-party tools—and data visualization techniques
  • Analyze a sample social media performance report and to identify key trends and opportunities for improved performance

With this session, you'll have your systems conversing and solving problems—with just a little guidance from you. Free up your time for more meaningful strategic and creative work with AI automation.

This how-to series requires a ChatGPT Plus, Claude PRO, or Gemini PRO account—your choice. As of August 1, 2025, each is $20 per month. Higher-tier, team, and enterprise accounts will work, too.

Headshot of Andy Crestodina

Meet Andy

Co-founder and CMO | Orbit Media

Andy Crestodina is the co-founder and chief marketing officer of Orbit Media, an award-winning, 50-person digital agency in Chicago. Over the past 20 years, Andy has provided digital marketing advice to over 1,000 businesses. He's also the author of Content Chemistry: The Illustrated Handbook for Content Marketing.

Headshot of Christopher S. Penn

Meet Chris

Chief Data Scientist | Trust Insights

Christopher S. Penn is an authority on analytics, digital marketing, and marketing technology. A recognized thought leader, best-selling author, and keynote speaker, he has shaped four key fields in the marketing industry: Google Analytics adoption, data-driven marketing, modern email marketing, and artificial intelligence/machine learning. As chief innovator of Trust Insights, he is responsible for the creation of products and services, creation and maintenance of all code and intellectual property, technology and marketing strategy, brand awareness, and research & development. He is the author of over two dozen marketing books including bestsellers such as AI for Marketers: A Primer and Introduction and Marketing White Belt: Basics for the Digital Marketer.

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