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Uncertainty Is Real. Opportunity Is Too.
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 | You Can't Measure AI ROI If You Can't Measure Marketing ROI
Tue, Apr 28, 2026 — Executive Takeaways Most mid-market companies lack the measurement foundation to evaluate AI — or any marketing investment. Hours saved, speed to market, and revenue realized are the three key AI ROI markers — baseline required. AI amplifies what's working. If measurement is broken, AI won't fix it. Real results start with a defined problem and a way to measure it — not the tool. 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.
Outsider Insights | What We’re Hearing from CEOs Right Now — And Why AI Keeps Coming Up
Wed, Mar 18, 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. Executive Takeaways AI accelerates clarity. It doesn’t fix broken data. Speed to confident decisions is the real competitive edge. Shared definitions matter more than more dashboards.. Governance comes before automation, alignment before acceleration.
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Outsider Insights | Agentic AI: What CEOs Need to Know Before They Invest
Wed, Feb 18, 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. Executive Takeaways Gen AI assists. Agentic AI acts, and requires a higher level of organizational readiness. AI-driven buyer research is reshaping vendor visibility before sales engagement begins. Agentic AI initiatives fail when layered onto unclear processes, weak data, or undefined business problems. Operational discipline, not technology adoption, determines whether AI becomes a scalable growth lever.
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.
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.
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.
Beating Industry Benchmarks
Fri, Jul 18, 2025 — In my previous blog, I discussed a fast way to assess relative marketing performance, and covered proven approaches to improving six industry benchmark-based Key Performance Indicators (reach, share, engagement, loyalty, pipeline, and progression) that can boost overall marketing effectiveness. Today, I’m going to review some of the key findings from recent research around Marketing benchmarks. I’ll select key metrics from each of these three benchmarks and their implications for optimizing marketing performance.
Rapid Marketing Performance Improvement
Mon, Jun 23, 2025 — With tariffs, the Middle East and trade tensions increasing the odds of a near-term recession and persistent inflation, it's more important than ever for CEO’s to increase marketing’s overall performance and the ROI of every marketing dollar spent. I created the Marketing Performance Index and Assessment to help CEO’s and their organizations quickly assess relative marketing performance. The Marketing Performance Assessment is an objective way of quantifying the impact of Marketing.