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Your AI Search Playbook - 6 Moves to Reclaim Visibility and Demand
Part 4 of our four-part series exploring how AI search is transforming visibility, SEO, and digital strategy - and what CEOs need to do now to stay competitive.
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.
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?
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.
The Revenue-Ready Marketing Playbook, Part 4: How a Shared Playbook Across Sales and Marketing Unlocks Value
Fri, May 2, 2025 — This is Part 4 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle. You’ve got a sharp Marketing team. An experienced Sales leader. Solid product-market fit. And yet, the customer experience feels disjointed. Campaigns generate leads that go quiet after handoff. Sales calls start from scratch, even when prospects have engaged with marketing content. Messaging shifts between touchpoints and the onboarding experience doesn’t match what was sold.
The Revenue-Ready Marketing Playbook, Part 3: How Marketing Can Deliver Predictable Outcomes
Fri, May 2, 2025 — This is Part 3 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle. In many boardrooms, the prevailing sentiment is "Marketing is a black box - effective in parts, but it's unclear which parts." That kind of uncertainty is surprisingly common. For many growth-stage businesses, marketing still feels like a gamble. You spend, you hope, you wonder if it worked.
The Revenue-Ready Marketing Playbook, Part 2: In a Noisy Market, Make Clarity Your Competitive Edge
Tue, Apr 22, 2025 — This is Part 2 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle. A CEO once said to me, “We know our product delivers real value. Our customers are happy. But when we show up in the market, it feels like we’re saying the same thing as everyone else.” That stuck with me, not just because it was honest, but because it’s common. In crowded markets, sounding the same is the fastest way to become invisible. Buyers tune out. Sales cycles drag. Margins shrink. And despite how strong your actual offering is, you keep getting boxed in as “just another option.”
The Revenue-Ready Marketing Playbook: Why Your Brand Is Your Most Powerful Compounding Asset
Tue, Apr 22, 2025 — This is Part 1 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle. Each chapter explores how to turn brand, positioning, operations, and customer experience into engines for measurable growth.