The Shift in Search: Perspectives from Top CMOs on the Future of Search, GEO & Discovery

We recently had the privilege of hosting some of the Bay Area’s sharpest marketing minds for an intimate dinner focused on a topic that’s rapidly reshaping digital strategy: Search.

But this wasn’t your standard SEO conversation. The marketers around the table are rethinking everything—from how buyers discover content to how websites should be structured in an AI-first world. Thank you to Jeff Otto (CMO, Riskified), Varun Kohli (CMO, Cequence), Janet Jaiswal (GVP, Marketing, Blueshift), Theresa Piasta (Customer Strategy, Cresta), Joseph Chong (CMO, Incode) , Kirti Dewan (CMO, Fiddler), Manish Gupta (CMO, LaunchDarkly), Aurelie Guerrieri (CMO, Data Dome), and Ricardo Cantu (Global Head of Growth, Incode) for joining us in this deeply thoughtful exchange.

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It’s clear that the future of search isn’t just about ranking higher—it’s about understanding buyer intent, surfacing the right message at the right time, and making your content work harder in a world where LLMs, not humans, are often the first to read your site.

Below are some of the key takeaways from the conversation, paired with our own POV from what we’re building at Webless—a platform designed for this new paradigm of content discovery and generative search.

1. From Keywords to Questions

The Insight
Search is no longer about optimizing for static keywords. It’s about matching buyer intent, often expressed in the form of natural language questions. “What questions should we rank for?” is becoming the new SEO strategy.

Webless POV
At Webless, we help companies move from a page-first to a question-first mindset. Our AI-powered semantic search listens to visitor questions in real time, then matches them to the most relevant content across your site—even if that content is buried across blogs, datasheets, or support pages. We also show you what your visitors are asking, so you know exactly which questions your content should answer next. Visitors of your website are the sample of your prospects in the market - so solve for visitors with right content, and you are solving it for prospects in the broad market.

2. First-Party Data Is the New Search Engine

The Insight
In a post-cookie world, marketers are leaning into first-party data—not just for ad targeting, but as the fuel for personalized, privacy-safe on-site experiences.

Webless POV
Webless uses in-session disclosures—what users ask, search, and click on—to personalize their journey instantly. Instead of guessing a visitor's intent based on referral data or firmographics, we let visitors self-declare their goals and challenges. This first-party signal allows our system to dynamically surface the right message, product, or CTA—without any tracking pixels or creepy profiling.

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3. Use GEO to Feed GEO

The Insight
If generative engines are already ranking and summarizing your content, why not feed them what they already reward? Several marketers are experimenting with structured, summary-style content built specifically for AI consumption.

Webless POV
We help companies create GEO-ready content automatically. Our platform identifies high-intent pages and suggests AI-friendly summaries, answers, and snippets that can be embedded directly on the page. It’s not just about ranking—it’s about ensuring your content is indexable, comprehensible, and reusable by LLMs. Every single page on your website can be optimized for GEO with help of webless generated summaries.

4. The Death of Glossaries, the Rise of FAQs

The Insight
Glossary pages are being deprioritized in SEO rankings. Meanwhile, FAQ-style content—which is question-led, concise, and semantically rich—is performing better with both traditional and generative engines.

Webless POV
We dynamically turn your content into a rich FAQ layer—no manual tagging required. By extracting questions from your pages and structuring them into a real-time, conversational layer, Webless ensures your site content is not only easier to navigate but also better aligned with how LLMs consume and summarize information.

5. robot.txt → llm.txt

The Insight
AI crawlers are becoming the new default readers of the web. Just like robots.txt guided traditional bots, marketers are now discussing llm.txt as a way to signal to LLMs what content to prioritize, summarize, or ignore.

Webless POV
We’re actively guiding customers through this shift—from sitemap-based SEO to LLM-optimized signaling. Our platform generates structured metadata, suggested llm.txt directives, and even summary snippets, making sure your site is ready for AI indexing. We believe this will soon be table stakes for modern content strategy.

6. Short-Form Content Makes a Comeback

The Insight
While long-form content still matters, snackable, high-signal content is emerging as the go-to format for AI-generated summaries and featured answers.

Webless POV
We help you mine your long-form content for the high-signal moments. Think of it as content atomization for the AI era: our tools extract key summaries, stats, and snippets from longer assets and make them searchable, findable, and reusable—both for your human visitors and AI agents.

7. RAG + Knowledge Graph = Precision

The Insight
Combining RAG (Retrieval-Augmented Generation) with structured data like knowledge graphs is enabling more accurate and brand-safe responses—especially in industries like SaaS, cybersecurity, and healthcare.

Webless POV
Our platform incorporates a light knowledge graph layer on top of your content—categorizing it by product, persona, funnel stage, industry, and more. When visitors ask a question, we use RAG techniques to pull from both unstructured content and structured metadata, delivering fast, relevant, and accurate responses grounded in your own source material.

8. Avoid Non-Summarizable Content

The Insight
Several leaders noted that interactive tools—like ROI calculators or PDF flipbooks—often get skipped by AI models. If it’s not readable or summarizable, it’s invisible.

Webless POV
We help customers audit their content for AI visibility. If it can’t be parsed, summarized, or reused, we flag it. More importantly, we help repackage complex content into AI-consumable formats—like Q&A cards, semantic highlights, or text overlays—that maintain their value without sacrificing discoverability.

Final Thoughts: The Shift Has Begun

The conversation around the table confirmed what we’ve been seeing in the market: the nature of web discovery is undergoing a radical transformation. Traditional SEO tactics are giving way to a new playbook—one grounded in generative engines, intent-first design, and AI-friendly content.

At Webless, we’re not just watching this shift—we’re building for it. Whether it's through semantic search, generative content discovery, or AI-powered personalization, we help B2B companies evolve their websites into living, learning systems that convert curiosity into action.

Want to learn more or join a future dinner? Reach out here.

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