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The Chief Outsider
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Outsider Insights | What We’re Hearing from CEOs Right Now — And Why AI Keeps Coming Up
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. |
Why the CEO-Led Growth Model Breaks at Scale
Tue, Feb 10, 2026 — Series Overview As companies grow, GTM breakdowns rarely show up as sudden failures. They emerge as friction. Progress slows, pipelines become less predictable, and confidence in forecasts declines, even as teams work harder and act with good intent. Written from both the marketing and sales lens, this six-part series, Building a Unified GTM Operating Model, explores why scale exposes weaknesses in informal GTM systems and how an intentional operating model restores clarity, alignment, and scalable growth. Executive Takeaways CEO-led, informal GTM models break predictably as scale introduces complexity. Early GTM failure shows up as friction, not collapse. Sales–marketing misalignment is a structural issue, not a performance problem. A unified GTM operating model is required to restore growth, confidence, and value.
What Can Chester Cheetah Tell You About Your Brand? Part Two
Fri, Aug 1, 2025 — We’ve already discussed how to define a brand in part one. Now, we are going to explore why the C-suite should care about its brand at all. It’s not just numbers, although that certainly is the end game. Remember that brand is the business. Like the business, brand is about being effective, meaning carving a position with a market that is highly productive financially and competitively, and efficient, meaning serving the market in as cost-efficient manner as possible. Brand helps maximize and expand return on investment.
What Can Chester Cheetah Tell You About Your Brand?
Fri, Jul 18, 2025 — Imagine an argument about whether Chester – yes, Chester of Cheetos fame – should be 2D or 3D. The debate raged in almost every corner of Frito-Lay headquarters at the time. There were strong opinions on both sides and an even more provocative discussion about the brand’s target audience. At the time, two of every three bags of Cheetos purchased were consumed by adults, not tweens and teens. So, the debate was fair, if inconvenient.
Why CEOs Must Be Active on Social Media: Building Trust and Authenticity with Customers
Wed, May 14, 2025 — I’ve seen firsthand how a CEO’s presence on social media changes how people view a company. Customers, employees, and potential hires want to know who’s steering the ship. When I show up online and share my perspective, the conversations become more genuine, and trust starts to build. It’s not about self-promotion – it’s about showing the real person behind the title.
Sales Velocity Model: A Tool for Growth Engine Mechanics
Wed, May 14, 2025 — Most companies deploy a sales “force”. Too often, their combined efforts are not meeting company growth expectations. Most CEOs would like a better growth engine, a larger sales pipeline, and more sales, but they struggle with exactly how to help their sales teams. Busy CEOs combined with people and process related complexities of Sales, often results in companies not being clear on the root cause of their growth engine problems.
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.”