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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.
Your AI Search Playbook - 6 Moves to Reclaim Visibility and Demand
Tue, Feb 3, 2026 — 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.
You’re Being Talked About (or Ignored) - Offsite Signals Drive AI Search Visibility
Fri, Jan 23, 2026 — Part 3 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. Executive Takeaways AI search engines pull data and content from across the web - not just your website. Brand mentions, reviews, and forum posts now shape how AI describes you. Reddit, G2, Quora, and even Amazon reviews influence AI-generated answers. Monitoring and managing offsite presence is now a strategic imperative.
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.
GEO – What it is and Why You Should Understand It
Fri, Jan 9, 2026 — Part 2 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. Executive Takeaways GEO is about optimizing for answers within AI search engines. Ranking well doesn’t guarantee visibility anymore – AI citations are needed too. Offsite reputation and mentions are just as critical as on-page SEO.
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.
AI Search is Here – And it’s Reshaping the Buyer Journey
Tue, Dec 16, 2025 — Part 1 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. Executive Takeaways Declining web traffic isn’t random - it’s a symptom of changing search behavior. AI search is already impacting over 25% of user journeys - and growing fast If you’re not being cited, you’re missing opportunities-period.
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.
Beyond the Buzzwords: How CEOs Can Build a Truly Resilient Business
Wed, Oct 22, 2025 — In every keynote, article, and boardroom conversation, “resilience” gets tossed around as the Holy Grail of leadership virtue. But resilience is more than just surviving economic turbulence—it’s about turning disruption into a competitive edge. Too many CEOs treat resilience as a slogan rather than a strategy. Real resilience is built in advance, not claimed during a downturn. It starts with clarity regarding where you are in the economic cycle, where you’re headed, and how to align your people and resources accordingly.
The Cost of Waiting: Why “Doing Nothing” Is the Most Expensive Strategy
Tue, Oct 7, 2025 — When markets shift, many CEOs adopt a dangerous mindset: Let’s wait and see. On the surface, it feels prudent, even safe. But hesitation quickly becomes the costliest default in leadership—a form of self-sabotage and an expensive compromise. Economic shifts don’t pause until you’re ready. By the time you’re confident the upturn is real—or the downturn has arrived—it’s too late to act decisively. Competitors who moved first have already secured the best opportunities. And you’ll be left wishing you had not waited.