Marketing Against The Grain

Episode: Using Perplexity AI to Reverse Engineer a $500M Marketing Strategy
Date: October 16, 2025
Hosts: Kipp Bodnar (HubSpot CMO), Kieran Flanagan (HubSpot SVP of Marketing)
Guest Speaker: Sam (HubSpot/AI enthusiast)

Episode Overview

This episode dives deep into how marketers can harness the power of Perplexity AI’s Comet browser to “steal” or reverse engineer the most successful marketing strategies from leading businesses. Sam demonstrates, in a practical and conversational manner, how reverse engineering—once a time-consuming task—can be automated and turbocharged with AI. Whether you’re an established marketer or a technical founder with little marketing know-how, Sam asserts this workflow can give you untapped insight and a tangible competitive edge.

Key Discussion Points & Insights

1. The Genesis of the Idea (01:04)

• Sam shares how frequently seeing Groons' Instagram ads sparked curiosity about their strategy.
• Instead of guessing or doing manual research, he uses Perplexity Comet to analyze the Groons website and uncover strategy details.

2. How Perplexity AI Comet Works (03:10)

• Browser Assistant Feature: You can ask questions in the browser, and the AI agent crawls through the live website and third-party sources to answer.
• Sam’s Example Prompt:
  “This company makes amazing personalized Instagram ads I always see. Can you explain how they do it, what tools they use?”
• AI Output: Lists Groons’ methods (creative testing, persona-driven messaging, rapid creative sprints, influencer/UGC programs, use of advanced ad creation tools) and specific technologies.

3. Extracting Tactical Insights (04:29)

• Tools and Tech Stack Uncovered:
  • Meta Ad Manager
  • Attribution: North Beam
  • AI Ad Creation: Icon, Foreplay, Atria
  • Influencer Management: Grin
  • Shopify ecosystem
• Reverse Engineering with AI:
  Sam explains how AI can even detect tools from source code and tracking codes on sites to provide actionable information.
• If you want to learn “how they really use AI ad generation in their strategy,” the AI assistant gives detailed breakdowns, like how Groons integrates Icon’s Ad GPT workflows and even an “AI Chief Marketing Officer.”

4. Applying Reverse Engineering to Any Company (05:55)

• Works for brands big (Nike) or small (Groons); can analyze overall site or specific product pages.
• Sam’s Shortcut (“/reverse”):
  • Pre-built prompt for extracting full strategic analysis from any web page.
  • Example: For Nike, outputs CTA, target audience, positioning, offer structure, funnel hypotheses, messaging, and conversion architecture.
• Especially valuable for non-marketers (sales or technical founders) to quickly decode top competitors’ approaches.

5. Conversion Architecture & Competitive Analysis (07:30)

• Understanding competitors’ conversion flows so you can create a “better and simpler” version for higher conversion rates.
• “There is literally like a hundred ways you can use this to actually grow your business in a really remarkable way and really make your marketing much stronger.” [Sam, 07:50]

6. Practical Extensions and Experimentation (08:46)

• Use with product pages, Instagram accounts—any digital marketing asset.
• Build your own experiments and playbooks based on real-time competitive intelligence.

7. Game-changing Speed of AI-Powered Analysis (08:25)

• What used to take days, now takes minutes.
• “If you literally just did this for a day, you would probably know more about your competition or the most admired brand's web and marketing strategies than most people working at those companies.” [Sam, 09:54]

Notable Quotes & Memorable Moments

• On the impact of incomplete data:

  “Using only 20% of your business data is like dating someone who only texts emojis. First of all, that's annoying. And second, you're missing a ton of context.” (HubSpot Host, 00:19)

• On rapid insight with Perplexity Comet:

  “What’s really cool is that the Perplexity Assistant breaks down their entire strategy of how they do Instagram ads.” (Sam, 02:50)

• On the value of AI in competitive intelligence:

  “You can now reverse engineer anybody's strategy… The fact that you can quickly and easily reverse engineer anybody's marketing strategy is remarkable.” (Sam, 08:46, 09:40)

• On democratizing expert-level analysis:

  “If you are maybe a technical founder or a sales founder. You don't know a ton about marketing. You can just go and do this for a bunch of relevant companies in your industry and get a deep understanding very quickly of how they're thinking about marketing…” (Sam, 06:30)

Important Timestamps

| Timestamp | Segment | |-----------|---------| | 01:04 | Origin story: Curiosity about Groons’ Instagram ads leads to AI-aided reverse engineering.
| 03:10 | Demonstration of Perplexity Comet’s browser assistant and prompt examples.
| 04:29 | Exploration of tools and how deeper tactical insights are surfaced.
| 05:55 | Application across companies (Nike, ServiceNow) with Sam’s custom shortcut prompt.
| 07:30 | Conversion architecture analysis and practical competitive applications.
| 08:25 | AI speeds up research: minutes instead of days.
| 09:54 | The “student of marketing” mindset—learning more than insiders.

Episode Takeaways

• Perplexity Comet empowers marketers of any experience level to deconstruct and adapt powerful marketing strategies almost instantly.
• Sam’s systematic approach—using prompts and browser assistants—lets users dig up everything from creative workflows to tech stack specifics.
• Reverse engineering is no longer a laborious, manual project; with AI and the right prompts, it becomes an everyday, game-changing habit.

Recommended Action:
Download Perplexity Comet, use or customize Sam’s “/reverse” prompt, and in minutes, gain actionable marketing strategies from your favorite or fiercest competitors.

(Jump to 03:10 for the live demo and to 05:55 for advanced applications!)