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AI Search is Here – And it’s Reshaping the Buyer Journey
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.
Beyond the Buzzwords: How CEOs Can Build a Truly Resilient Business
Wed, Oct 22, 2025 — In every keynote, article, and boardroom conversation, “resilience” gets tossed around as the Holy Grail of leadership virtue. But resilience is more than just surviving economic turbulence—it’s about turning disruption into a competitive edge. Too many CEOs treat resilience as a slogan rather than a strategy. Real resilience is built in advance, not claimed during a downturn. It starts with clarity regarding where you are in the economic cycle, where you’re headed, and how to align your people and resources accordingly.
The Cost of Waiting: Why “Doing Nothing” Is the Most Expensive Strategy
Tue, Oct 7, 2025 — When markets shift, many CEOs adopt a dangerous mindset: Let’s wait and see. On the surface, it feels prudent, even safe. But hesitation quickly becomes the costliest default in leadership—a form of self-sabotage and an expensive compromise. Economic shifts don’t pause until you’re ready. By the time you’re confident the upturn is real—or the downturn has arrived—it’s too late to act decisively. Competitors who moved first have already secured the best opportunities. And you’ll be left wishing you had not waited.
Becoming the Issachar CEO: Leading with Foresight in a Time of Uncertainty
Tue, Sep 30, 2025 — It’s not every day that a C-suite leader turns to 1 Chronicles for advice, but there’s something here for us. 1 Chronicles chapter 12 describes each of the tribes of the nation of Israel as they moved their allegiance from the house of Saul to the newly crowned King David. The scripture recounts an impressive array of warrior clans ready to fight for their new king, until it reaches the tribe of Issachar, described in verse 32 as “men who had understanding of the times, to know what Israel ought to do.”
From Recovery to Recession: A CEO’s Guide to Thriving Through Economic Shifts
Tue, Sep 9, 2025 — When markets shift—and they always do—the winners are those who don’t wait to react. They move first, and fast. No matter which of the four cycles you’re currently experiencing, one constant remains true: waiting for things to be more favorable is a bad strategy. Additionally, doing nothing is not an option. Companies that anticipate, plan, and act in alignment with their current business phase can maintain resilience, capture opportunities, and outperform competitors who simply “wait it out.”
From Economic Insight to Growth Strategy: What CEOs Should Do Now
Tue, Aug 26, 2025 — At our most recent CEO Growth Talks, I spoke with Taylor St. Germaine, Senior Economist at ITR Economics. The timing couldn’t have been better — the latest GDP numbers had just been released, and Taylor broke down what they mean for CEOs planning growth. As always, ITR brought a clear and fact-based perspective. The economy is growing. Consumer spending is strong. And while some industries are facing headwinds, opportunities abound for leaders who are ready to act. But the real question for CEOs isn’t just what the economy looks like. It’s: how do you prepare your business to grow in this environment — and the one coming next?
What Can Chester Cheetah Tell You About Your Brand? Part Two
Fri, Aug 1, 2025 — We’ve already discussed how to define a brand in part one. Now, we are going to explore why the C-suite should care about its brand at all. It’s not just numbers, although that certainly is the end game. Remember that brand is the business. Like the business, brand is about being effective, meaning carving a position with a market that is highly productive financially and competitively, and efficient, meaning serving the market in as cost-efficient manner as possible. Brand helps maximize and expand return on investment.
What Can Chester Cheetah Tell You About Your Brand?
Fri, Jul 18, 2025 — Imagine an argument about whether Chester – yes, Chester of Cheetos fame – should be 2D or 3D. The debate raged in almost every corner of Frito-Lay headquarters at the time. There were strong opinions on both sides and an even more provocative discussion about the brand’s target audience. At the time, two of every three bags of Cheetos purchased were consumed by adults, not tweens and teens. So, the debate was fair, if inconvenient.
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part Two
Thu, Jul 17, 2025 — In Part One, we established the critical groundwork: vision clarity and deep market understanding. Now it’s time to convert strategy into results. This section of the playbook takes you through the essential steps to build, activate, and scale your go-to-market initiatives.