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Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI
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.
5 AI Trends Every CEO Must Act On
Mon, Sep 15, 2025 — Earlier this year, I shared takeaways from Mary Meeker’s Internet Trends Report, which showed how AI is reshaping business at a macro level. Building on that, Google Cloud’s 2025 AI Trends Report highlights five forces that will directly impact companies in the year ahead. AI is no longer experimental. It is restructuring markets, reshaping customer expectations, and redrawing competitive boundaries. Here are five AI trends CEOs are preparing for now:
From Economic Insight to Growth Strategy: What CEOs Should Do Now
Tue, Aug 26, 2025 — At our most recent CEO Growth Talks, I spoke with Taylor St. Germaine, Senior Economist at ITR Economics. The timing couldn’t have been better — the latest GDP numbers had just been released, and Taylor broke down what they mean for CEOs planning growth. As always, ITR brought a clear and fact-based perspective. The economy is growing. Consumer spending is strong. And while some industries are facing headwinds, opportunities abound for leaders who are ready to act. But the real question for CEOs isn’t just what the economy looks like. It’s: how do you prepare your business to grow in this environment — and the one coming next?
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part Two
Thu, Jul 17, 2025 — In Part One, we established the critical groundwork: vision clarity and deep market understanding. Now it’s time to convert strategy into results. This section of the playbook takes you through the essential steps to build, activate, and scale your go-to-market initiatives.
AI Isn’t a Replacement—It’s an Accelerator: How SMBs Can Use AI to Elevate Human Performance Across the Organization, Part 2
Thu, Jun 26, 2025 — AI as an Executive and Organizational Force Multiplier In Part 1, we explored how AI streamlines execution in outward-facing functions like marketing, sales, and customer service. Now it’s time to turn inward. In this second half, we’ll examine how AI empowers internal operations, drives better financial strategy, and helps executive leaders see farther and act faster—without sacrificing the human qualities that make a business thrive.
Go Time? Or Just Another Head Fake? How Mid-Market CEOs Should Move Forward Now
Wed, Jun 25, 2025 — Six months ago, we diagnosed a condition gripping mid-market companies across the country: Waitflation. Leaders were holding back—not because of financial hardship, but because of economic ambiguity. Interest rates were high, forecasts were fuzzy, and confidence was low. The result? A national game of “wait and see.” Now, as we enter a volatile summer, it’s time to ask: Is it go time?
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part One
Mon, Jun 23, 2025 — Every CEO knows this nightmare scenario: Your team spent months crafting the "perfect" go-to-market strategy, only to watch it crumble during execution. Resources hemorrhage, timelines slip, and while you're still troubleshooting internal alignment issues, competitors are capturing the market opportunity you identified first.
AI Isn’t a Replacement—It’s an Accelerator: How SMBs Can Use AI to Elevate Human Performance Across the Organization
Fri, Jun 20, 2025 — We’re in the midst of a generational shift—one where artificial intelligence is reshaping how we work, how we serve customers, and how we think about the roles of humans in business. But here’s the reality I’ve seen across dozens of companies: AI is not a silver bullet, and it’s not a pink slip. It’s a power tool—one that requires a skilled operator, a clear use case, and the right safety measures in place.
Winning the Fraud and Cybersecurity Race: A Go-to-Market Blueprint for Competitive Edge
Thu, Jun 5, 2025 — Fraud and cybercrime have become a systemic, trillion-dollar drag on the global economy—but the fight to turn the curve is more than a market opportunity. Over the past few years, I have worked alongside cybersecurity and fraud-management teams in government, banking, and payments, and nothing is more satisfying than seeing a new solution stop a romance scam or prevent a pensioner from losing their life savings.