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Are You Building a Business That's Ready to Scale - or Just a Business That Has Had Great Growth?
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.
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.
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.