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Outsider Insights | Agentic AI: What CEOs Need to Know Before They Invest
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
| Executive Takeaways |
| Gen AI assists. Agentic AI acts, and requires a higher level of organizational readiness. |
Why the CEO-Led Growth Model Breaks at Scale
Tue, Feb 10, 2026 — Series Overview As companies grow, GTM breakdowns rarely show up as sudden failures. They emerge as friction. Progress slows, pipelines become less predictable, and confidence in forecasts declines, even as teams work harder and act with good intent. Written from both the marketing and sales lens, this six-part series, Building a Unified GTM Operating Model, explores why scale exposes weaknesses in informal GTM systems and how an intentional operating model restores clarity, alignment, and scalable growth. Executive Takeaways CEO-led, informal GTM models break predictably as scale introduces complexity. Early GTM failure shows up as friction, not collapse. Sales–marketing misalignment is a structural issue, not a performance problem. A unified GTM operating model is required to restore growth, confidence, and value.
Your AI Search Playbook - 6 Moves to Reclaim Visibility and Demand
Tue, Feb 3, 2026 — Part 4 of our four-part series exploring how AI search is transforming visibility, SEO, and digital strategy - and what CEOs need to do now to stay competitive.
You’re Being Talked About (or Ignored) - Offsite Signals Drive AI Search Visibility
Fri, Jan 23, 2026 — Part 3 of our four-part series exploring how AI search is transforming visibility, SEO, and digital strategy - and what CEOs need to do now to stay competitive. Executive Takeaways AI search engines pull data and content from across the web - not just your website. Brand mentions, reviews, and forum posts now shape how AI describes you. Reddit, G2, Quora, and even Amazon reviews influence AI-generated answers. Monitoring and managing offsite presence is now a strategic imperative.
The Evolution of B2B Selling: Focus on Helping Customers Buy
Thu, Jan 15, 2026 — Many B2B companies are experiencing longer sales cycles, declining win rates, and increasingly unreliable forecasts—not because their sales teams are ineffective, but because their customers are struggling to buy. Executive Takeaways B2B buyers face overwhelming complexity, not a lack of information. Long sales cycles and no-decisions often reflect buyer indecision, not sales failure. Winning sellers focus on boosting buyer confidence, not pitching products. Helping customers buy is now the key to competitive differentiation.
Outsider Insights | Beyond the Sale—Why CEOs Are Turning Attention to Retention and Expansion
Wed, Jan 14, 2026 — Outsider Insights Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
GEO – What it is and Why You Should Understand It
Fri, Jan 9, 2026 — Part 2 of our four-part series exploring how AI search is transforming visibility, SEO, and digital strategy - and what CEOs need to do now to stay competitive. Executive Takeaways GEO is about optimizing for answers within AI search engines. Ranking well doesn’t guarantee visibility anymore – AI citations are needed too. Offsite reputation and mentions are just as critical as on-page SEO.
Outsider Insights | What We Learned Helping CEOs Grow in 2025
Mon, Jan 5, 2026 — Outsider Insights Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
AI Search is Here – And it’s Reshaping the Buyer Journey
Tue, Dec 16, 2025 — Part 1 of our four-part series exploring how AI search is transforming visibility, SEO, and digital strategy - and what CEOs need to do now to stay competitive. Executive Takeaways Declining web traffic isn’t random - it’s a symptom of changing search behavior. AI search is already impacting over 25% of user journeys - and growing fast If you’re not being cited, you’re missing opportunities-period.
Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Mon, Nov 3, 2025 — Outsider Insights Across Chief Outsiders, we talk to hundreds of CEOs every month. In this new series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.