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Marketing's Lost Generation: Why Execution Outpaced Strategy
This blog is part of Chief Outsiders’ Marketing Leadership for CEOs series, an ongoing examination of the critical dimensions of Marketing (the capital “M” is intentional, as you’ll see) that every CEO needs to understand.
Your Paid Search Budget Is Buying Less. Here's Why.
Fri, Aug 14, 2026 — Executive Takeaways Paid search costs reached a six-year high while clicks and impressions declined. This is a structural shift, not a temporary correction, and B2B is disproportionately affected. AI Overviews appear on 54% of tracked B2B keywords versus 22% for B2C. Google's recent search redesign signals these pressures will intensify. The companies adapting fastest are shifting from click volume to conversion quality. Part 2 of our four-part series on the evolving AI search landscape and what B2B leaders need to know to stay competitive.
Vistage Chairs: Is Your Member’s Marketing Really Working? Ask These 5 Questions.
Tue, Aug 11, 2026 — Executive Takeaways Most CEOs challenge every capital investment but can't say with confidence whether their marketing is working. More leads isn't better marketing. Better customers are. If sales and marketing are blaming each other, the CEO hasn't asked the right question. The real measure isn't what marketing produced. It's what it changed about the future economics of the business.
The Four Mistakes Founder-Led Companies Make Building a Revenue Organization
Tue, Aug 11, 2026 — Executive Takeaways The commercial function that got you to $10M–$15M was built for that stage. It doesn't automatically scale to the next one. Most founders don't see the gap from the inside. Buyers will see it immediately. Seven diagnostic signals reveal whether your revenue engine is built to scale — or just built for today. The earlier you find the gaps, the easier they are to close.
The Gap Between AI Output and Real Marketing Leadership
Thu, Aug 6, 2026 — Executive Takeaways AI can inform marketing strategy. It cannot own it, defend it, or answer for it when it fails. AI sounding right without the context to actually be right is the real risk. Trade-offs, risk calls, and accountability are executive work. AI can't take any of the three off your plate. Leadership owns the outcome, not the AI. A lot of CEOs are starting to ask the same question, even if they don't always say it this directly: if AI can build a strategy deck, suggest a campaign, analyze competitors, and hand back polished recommendations in seconds, why keep paying for a CMO?
The 90-Day GTM Transformation Roadmap: Building the GTM Operating Model While Running the Business
Thu, Aug 6, 2026 — Executive Takeaways The CEO must be the architect and champion of the GTM model — not its operator. Only the CEO has the cross-functional authority to make a unified GTM model stick. If the model only works when you're in the room, it's not a system. When it's working, your calendar proves it.
Are You Building a Business That's Ready to Scale - or Just a Business That Has Had Great Growth?
Mon, Jul 27, 2026 — Executive Takeaways The commercial function that got you to $10M–$15M was built for that stage. It doesn't automatically scale to the next one. Most founders don't see the gap from the inside. Buyers will see it immediately. Seven diagnostic signals reveal whether your revenue engine is built to scale — or just built for today. The earlier you find the gaps, the less expensive they are to close. There is a version of business success that feels like momentum but isn't quite there yet.
Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt
Fri, Jul 24, 2026 — Executive Takeaways Sales reps focus on what they're paid and measured on, even if that strays from business strategy and goals. Many compensation plans and account structures quietly reward protecting revenue, not creating it. Adding a quota target without changing the underlying structure just adds pressure, not pipeline. Fixing this starts with the comp plan and account map, not a pep talk about hustle. 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.
The AI Search Gap Between Buyers and Brands Just Got Wider
Fri, Jul 24, 2026 — Executive Takeaways B2B buyer AI adoption hit 94%, and company readiness didn't keep pace. The #1 organic ranking now captures under 2% of AI Overview searches. Google Gemini's chatbot share jumped 48% in a single month. The gap isn't awareness anymore. It's execution, and it's getting more expensive to ignore. Buyers have moved to AI search. Most companies haven't caught up.
What Is Marketing, Really? Why Founders and CEOs Must Lead the Most Misunderstood Function in the Business
Thu, Jul 9, 2026 — Executive Takeaways Marketing is a core enterprise capability, not a support function, and deserves the same CEO-level engagement as Finance and Operations. Without a unifying system, individually reasonable decisions accumulate into random acts of marketing. Modern tools make execution faster, but they don't create strategic clarity, so the gap between activity and alignment keeps widening. CEOs can't delegate marketing entirely. Leading it means ensuring insight, strategy, and execution stay connected. This blog is part of Chief Outsiders’ Marketing Leadership for CEOs series, an ongoing examination of the critical dimensions of Marketing (the capital “M” is intentional, as you’ll see) that every CEO needs to understand.