Found in AI Ep 8: How Bottom-of-Funnel Content Wins in AI Search (with Usama Khan)

ChatGPT’s Search Index, llms.txt Confusion & the Rise of AI Shopping Found in AI: AI Search Visibility, SEO, & GEO

Send us Fan Mail📬 You like this podcast? You’ll love the newsletter.Join the weekly The Visibility Report: subscribeIn this Found in AI news update, Cassie Clark breaks down Peec AI’s research into OpenAI’s Labrador retrieval index, including the separate indexes identified for web content, news, shopping, YouTube, PDFs, and more.Then, we look at Common Crawl’s analysis of more than 584,000 llms.txt files and what it tells us about the confusion surrounding llms.txt, robots.txt, and AI crawler access.Finally, Microsoft is preparing businesses for a future where AI agents don’t just help consumers discover products — they help choose and buy them. Microsoft’s latest agentic commerce guidance shows why structured, accurate, and current product data could become critical as AI moves from answering questions to taking action.In this episode:What Peec AI discovered about ChatGPT’s Labrador search indexWhy ranking in Bing isn’t a proxy for ChatGPT visibilityHow freshness appears within ChatGPT’s retrieval infrastructureOpenAI’s experiments with its own shopping indexWhat Common Crawl learned from 584,107 llms.txt filesThe difference between llms.txt and robots.txtWhy llms.txt does not control AI crawler accessMicrosoft’s recommendations for preparing for agentic commerceWhy structured product data matters when AI agents are shoppingThe difference between AI visibility and agent readinessWhy businesses should prepare for AI discovery even while the technology continues to changeSourcesPeec AI: “ChatGPT Built Its Own Search Index”Search Engine Journal: “Common Crawl Finds Widespread Confusion Around llms.txt & robots.txt”Microsoft Advertising: “How Businesses Win When AI Does the Shopping”–Cassie Clark is an AI search visibility consultant and a fractional content strategist for startups and enterprise brands. If that sounds like the kind of help you're looking for, email me at cassie@cassieclarkmarketing.com. Or request your AI Search Visibility Audit: https://cassieclarkmarketing.com/ai-search-visibility-audit/
  1. ChatGPT’s Search Index, llms.txt Confusion & the Rise of AI Shopping
  2. Google Is Moving From AI Search to AI Agents
  3. Is Your Best Content Invisible to AI Search?
  4. Google AI Mode Gets More Links + Yahoo Scout’s AI Search Push
  5. Does YouTube Help You Show Up in AI Search?

In this episode of Found in AI, I sit down with Usama Khan, a B2B SaaS content strategist, to unpack how bottom-of-funnel content is evolving in the age of AI search—and why clarity and real customer insight matter more than ever.

We cover:

  • Why middle- and bottom-of-funnel content now drives the majority of AI search visibility
  • The three proven formats every startup should prioritize: category, comparison, and jobs-to-be-done keywords
  • How to use sales calls and product demos to write content that actually converts
  • Why generic messaging confuses both readers and large language models
  • The growing role of authority signals like Reddit mentions and G2 reviews in AI visibility

If you’ve been wondering how to adapt your content strategy for an AI-first search world — and how to make bottom-of-funnel content work harder than ever — this episode is for you.

Mentioned in this episode:

  • Bottom-of-funnel content frameworks
  • Category, comparison, and alternative pages
  • Jobs-to-be-done keyword research
  • Content pyramid model (via Animals)
  • AI search visibility metrics and authority signals

Transcript: How Bottom-of-Funnel Content Wins AI Search

Cassie Clark

Welcome back to Found in AI, the podcast helping get your brand found in AI search. I’m your host, Cassie Clark — content strategist and CMO of ThoughtTree.

This week, I sat down with Usama Khan, a B2B SaaS content strategist who’s spent years perfecting bottom-of-funnel content that actually converts.

We talked about what’s changing in AI-powered search, why clarity of messaging matters more than ever, and how startups can use comparison and alternative pages as some of their most powerful growth assets.

Here’s part of that conversation.

So, Usama — tell me about you. Give me a brief intro.


Usama Khan

Sure. I’ve been in the content marketing industry for about seven years now and shifted to B2B SaaS around three years ago. Since then, I’ve been working with startups and enterprises on content marketing, SEO, and writing — specifically middle- and bottom-of-funnel content.

I was doing that long before AI really took off, so it was a smooth transition once LLMs and GEO became part of the conversation. I’ve just continued working in that space, often collaborating with SEO agencies as well.


Cassie Clark

Yeah, we’ve been calling it the “alphabet soup” — SEO, GEO, AIO.


Usama Khan

Yeah, there are a lot of terms to keep track of now.


Cassie Clark

I’m not sure anyone has landed on the perfect one yet, but they’re all floating around.

I’ve also been in content for a while, but when I ask these questions, just pretend I know nothing about content marketing. They might sound a little silly — but we’re going somewhere with them, I promise.

So when you say bottom-of-funnel content, what does that mean to you? And how has that definition shifted in the age of AI search?


Usama Khan

Bottom-of-funnel content targets people who are already problem- and solution-aware.

When I say bottom of the funnel, I don’t just mean pricing pages or “X versus Y” posts. I like to divide this into three proven formats:

  1. Category keywords — for example, “best CMMS software for SMBs.” These are people who know their problem and are now looking for a solution.
  2. Comparison and alternative pages — like “HubSpot vs Salesforce” or “Monday.com alternatives.”
  3. Jobs-to-be-done keywords — for instance, if you’re an HR software, you might target “how to manage employee time off,” then present your product as the solution.

Cassie Clark

I was just talking about jobs-to-be-done with someone last week. A lot of guests mention the rise of how-to content. Are you seeing more clients request that type of content?


Usama Khan

Not necessarily. It’s still a valid strategy because people always have problems they’re searching to solve.

What I’m noticing from my clients is more focus on category keywords and, increasingly, on comparison and alternative pages. There’s still a mix of how-to and jobs-to-be-done keywords, but not a huge uptick.

However, what really helps is collaborating with internal teams — product, sales, customer success. Talking with them gives deep insight into what your target audience actually struggles with. Then, when you conduct keyword research informed by those insights, you uncover strong opportunities for jobs-to-be-done keywords you might otherwise miss.

That’s something I always emphasize, and it consistently works well for my clients.


Cassie Clark

So why do you think so many companies struggle with bottom-of-funnel content right now? Is it a strategy problem or a messaging problem?


Usama Khan

I wouldn’t say they’re all struggling, but one common issue is publishing bottom-of-funnel pages just for the sake of it.

When I consult with clients, I focus on being specific. Before creating a comparison page like “HubSpot vs Salesforce,” I talk with internal teams to understand:

  • What are those competitors lacking that your product does better?
  • What additional features do you offer?
  • How do those features serve your audience’s workflows?

The piece should be guided by internal knowledge — not just surface-level SERP research.

It’s time-consuming and resource-heavy, which is why companies without the right budget or processes tend to struggle.


Cassie Clark

That makes sense — it does take time. For the type of content you’re describing, how long would you say it takes to create one piece?


Usama Khan

The main challenge is aligning with internal teams because they’re often busy. But once that’s done, about a week is enough to produce a high-quality bottom-of-funnel piece.


Cassie Clark

Let’s talk about formats. What’s one underrated content format startups should be investing in right now — if they have the budget or bandwidth? Case studies? ROI calculators?


Usama Khan

ROI calculators are great, but they’re more of a lead magnet.

I’d say focus on use-case-driven content. Make sure every use case or key feature has its own page and ties back to a keyword.

People are actively searching for solutions to specific problems. Being detailed and precise in addressing those opportunities pays off.


Cassie Clark

If a startup has limited resources, what’s the first bottom-of-funnel asset you’d tell them to create?


Usama Khan

That depends on the landscape, but I’d start with comparison and alternative pages — “X vs Y” or “X alternatives.”

These readers are already using a similar solution but are looking to switch — maybe due to budget, features, or performance gaps. They’re ready to convert.

If you can produce solid content that helps them make that switch, you’ll capture real intent.


Cassie Clark

Have you seen examples of your content being surfaced in AI answers?


Usama Khan

Yes, definitely.

There’s a lot of hype around LLMO and GEO, but I like to think of it as a content pyramid — and Animals has a great blog post about this.

The pyramid has three layers:

  1. A strong SEO foundation — fast, technically sound websites.
  2. Context-rich, product-centric content — mostly middle- and bottom-of-funnel. Top-of-funnel content is far less effective today. AI Overviews and tools like Perplexity may still surface it, but conversions are minimal.
  3. Trust and authority signals — these amplify credibility. We used to rely on backlinks, but now things like Reddit mentions, G2 reviews, and brand visibility play a major role.

Cassie Clark

Yes, that’s coming up a lot when I talk with other guests — get your G2 reviews ready, make sure you’re visible on Reddit, all of that.


Usama Khan

Exactly — especially Reddit.

Every other post on my LinkedIn feed is about it. I’m still undecided about how sustainable Reddit really is, though. The community can sense self-promotion a mile away.

If you’re going to talk about your product there, it has to come from genuinely helping people — adding value 95% of the time and maybe mentioning your tool the other 5%. Even then, there’s risk and it’s really rented space.

We’ll have to see whether it remains a viable long-term strategy within SEO and AI ecosystems.


Cassie Clark

When I write comparison pages, I often go straight to Reddit for research.

Aside from working with internal teams, what else do you do to make sure those pages are as accurate as possible?


Usama Khan

Whenever we have sales calls, I record them and store them in my own knowledge hub.

When discussing a new topic, clients often walk me through the product again — like a mini demo showing exactly how a workflow operates.

That helps me create accurate content and often gives me material like screenshots or GIFs to include in the piece.


Cassie Clark

That’s a really smart idea — doing live walkthrough demos with clients.


Usama Khan

Yep. When I onboard new clients, we do an 80- to 90-minute demo of all main features. They also share recordings of their sales calls, which provide additional insights.

Then, when I’m writing something very specific — like “how to manage employee time off” — I’ll schedule a short call so they can show me exactly which features support that use case.


Cassie Clark

Let’s switch gears and talk about AI search. Do you think AI makes clarity of messaging more important than ever, since both machines and buyers are processing information faster?


Usama Khan

Absolutely. Clarity is everything.

If you’re writing about something broad like “best CRM software,” smaller brands won’t rank. But if you’ve done your research and know your audience — say your CRM is perfect for small law firms with fewer than 30 employees — that specificity gives you a real chance to appear in AI-powered results.

Many brands still have confusing messaging — one thing on their homepage, something totally different on a product page. That inconsistency throws off both users and large language models.


Cassie Clark

Yeah, so being as clear and specific as possible really seems to be the way to go. Have you seen examples of companies using overly complex messaging and how it’s hurting performance?


Usama Khan

Yes. I worked with a client that started as a contact-center solution and later expanded into enterprise software — but their messaging never caught up.

All their pages still focused on contact centers, so they ranked there but completely missed enterprise-related queries.

Covering a topic in depth, with supporting subtopics — the good old topic cluster approach — still matters. It helps signal to search engines and LLMs that your content is authoritative and complete.


Cassie Clark

It seems like SEO fundamentals still apply even in AI search.


Usama Khan

Exactly.

A study by Grow & Convert found that if your page ranks in Google’s top 10, you have roughly a 67-77% chance of being mentioned in AI summaries. In the top 3, that jumps to 72-82%.


Cassie Clark

I believe that. AI search just adds another layer to a well-rounded SEO strategy.

So with that in mind, what skills should marketers build now to keep bottom-of-funnel content effective as AI evolves over the next few years?


Usama Khan

Marketers need to go beyond surface research.

Don’t just read the top five articles. Really understand your audience’s problems by listening to sales calls, talking to customer service and product managers, and collecting firsthand insights.

Then use that information to position your product as the solution to those specific problems.

The more specific and detailed your content, the better it will perform — both for search and for your audience.


Cassie Clark

That was Usama Khan on how bottom-of-funnel content supports your AI search strategy.

Here’s what you can do today to implement his insights:

Before you write another bottom-of-funnel piece, talk to your internal teams. Ask sales what questions they hear most, and ask product what truly differentiates your solution. Then build your next comparison or alternative page around those real conversations — not just keyword data.

That’s how you start creating content that earns trust, converts, and shows up in AI search engines.

If you want to make that process a little faster, check out ThoughtTree — an AI workspace that lets you save and reuse templates to repurpose insights from sales calls, interviews, and research.

We’re still in beta and looking for honest opinions from marketers who create every day. You can sign up at thoughttree.io and give it a try.

And if you’re ready to bring this kind of strategy to your own brand, connect with me — Cassie Clark — on LinkedIn or at cassieclarkmarketing.com.

Thanks for listening to Found in AI. I’ll see you next week.

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