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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.
AI Strategy for Financial Services CEOs: Why “Good Enough” is no Longer Enough
Mon, Feb 23, 2026 — AI in financial services has moved from lofty claims about AI's use to being at the center of the growth conversation, shaping how you compete, run, and stay trusted. Margins are under pressure as customers benchmark you against their best digital experiences, whether they are opening a checking account, redeeming loyalty points, disputing a card charge, or seeking hardship help.
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.
Why Your Messaging Isn’t Converting (and How to Fix It)
Thu, Aug 14, 2025 — After working with organizations of all sizes— from small businesses to Fortune 500 giants—one difference stands out: large, successful companies consistently invest in clear, concise, and emotionally compelling messaging that motivates their customers to act. Small and mid-sized businesses (SMBs) often start executing marketing and sales tactics — SEO, SEM, email campaigns, publicity, trade shows — before they have compelling messaging. Their messaging is often focused on what the company does, rather than what motivates the customer.
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.
Growth Hurts. Let it.
Wed, May 14, 2025 — “Don’t Risk Too Little. Don’t Rescue Too Soon” – the growth lesson I learned outside the boardroom. My son once played striker in a school tournament. With minutes left and his team trailing, he broke through the defense and had a clean look at the goal. He hesitated, and the shot went wide.
Tariffs and Your Next Chapter | Selling Through Tariffs: Avoiding the Pricing Traps
Tue, Apr 8, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
A CEO’s Guide to Marketing Performance | Measuring Performance (and Underperformance)
Thu, Feb 6, 2025 — Part 3 of A CEO's Guide to Marketing Performance In the marketing world, performance is the difference maker - not experience, expertise, effort, or endurance, just results. This article is about how to address underperformance in the three major measurement components (Market Presence, Brand Strength, and Pipeline Health), and six key performance indicators (reach, share, engagement, loyalty, pipeline, and progression).