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The 90-Day GTM Transformation Roadmap: Building the GTM Operating Model While Running the Business
| Executive Takeaways |
| The CEO must be the architect and champion of the GTM model — not its operator. |
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.
When the Numbers Still Look Fine, Look Harder
Mon, Jul 6, 2026 — Revenue Can Be Late to Tell the Truth Without a compass, course correction isn't really an adjustment. Too often, a company can drift while the scorecard still looks respectable. But underneath the dashboard, buying behavior may already be changing. Customers take longer to decide. Procurement gets more involved. Good prospects ask harder questions. Deals that used to move cleanly now need another approval, discount, or proof point. Early warning signs rarely show up with a siren attached.
Where Is Growth Coming From? A Playbook for Mid-Market CEOs
Thu, Jul 2, 2026 — The headlines say one thing. The data says something more nuanced. Here's what mid-market CEOs should actually be paying attention to right now. This two-part series from Chief Outsiders Founder & CEO Art Saxby explores what the data actually shows about CEO confidence, why this moment is different from past disruptions, and where mid-market companies are finding real growth opportunities right now.
Uncertainty Is Real. Opportunity Is Too.
Mon, Jun 15, 2026 — The headlines say one thing. The data says something more nuanced. Here's what mid-market CEOs should actually be paying attention to right now. This two-part series from Chief Outsiders Founder & CEO Art Saxby explores what the data actually shows about CEO confidence, why this moment is different from past disruptions, and where mid-market companies are finding real growth opportunities right now.
Outsider Insights | Google Just Declared the Search Box Dead: What CEOs Need to Know
Mon, Jun 15, 2026 — Executive Takeaways Google just redesigned Search for the first time in 25 years. 94% of B2B buyers use AI to research vendors before your sales team knows they exist. The companies earning AI citations share one thing: content written to inform, not to sell. 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.
Building a Cohesive C-Suite: How to Align Your Executive Team for Success
Fri, Jun 12, 2026 — Executive Takeaways A high-performing C-suite that doesn't function as a team is a hidden growth tax. If your executives describe the strategy differently, that gap shows up in your results. Alignment comes from operating rhythm, not offsites. Better-aligned executives. Same team. Very different results. When CEOs talk about growth, they usually focus on markets, products, and funding. What derails them more often is something closer to home: a strong group of executives that never quite functions as a true team. You feel it in slow decisions, mixed messages to the organization, and initiatives that lose momentum once they leave the last executive meeting.