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Recent Posts
Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
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.
Think Like Your Customer: 8 Cognitive Biases Every CEO Should Know
Mon, Aug 25, 2025 — Human beings like to think we make decisions logically. But research in behavioral science and neuroscience tells a different story: up to 95% of decisions are made unconsciously, then justified rationally. Cognitive biases shape every decision, often before logic enters the picture. These shortcuts drive customer responses to marketing, pricing, and branding, sometimes in ways that defy prediction.
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.
8 Strategic Moves to Grow Your Business with AI
Wed, Jun 18, 2025 — Top takeaways and action items from Mary Meeker’s 2025 AI Trends Report Generative AI is accelerating at a pace we've never seen before. ChatGPT, for example, reached 800 million users in just 17 months—far faster than the 11 years it took Google Search to hit similar annual query volumes. Tech giants are pouring hundreds of billions into AI infrastructure, making these tools cheaper, faster, and more accessible than ever before.
AI Marketing Trends Every CEO Should Know
Tue, Jul 16, 2024 — As artificial intelligence rapidly transforms the marketing landscape, companies can deploy smarter, faster, and more efficient marketing strategies. With AI tools and capabilities evolving at a breakneck pace, staying on top of the latest trends is crucial for CEOs looking to gain a competitive edge. Based on HubSpot's AI Trends for Marketers report, here are the top AI trends shaping the future of marketing for companies of all sizes and stages.
2019 Top Internet Trends and How They Impact Your Business
Tue, Jun 25, 2019 — For at least the past decade, developments in digital marketing – and technology in general – have served to disrupt virtually every industry. Whether you manufacture a product or deliver a service, your business undoubtedly has been roiled by digital developments, and their impact on the expectations – and buying behavior – of your customer base. Keeping apace with forthcoming developments can help any business better prepare for what’s to come – altering practices to successfully navigate this digital-first world.
The Top 12 Internet Trends Executives Should Know About in 2018
Wed, Jun 6, 2018 — For business executives, staying relevant in this time of innovation and rapid technological advancement can be challenging. Thankfully, we can leverage consumer and marketplace data to help our companies optimize products and services. One of the premier analytical reports on emerging business-related trends, Mary Meeker’s annual Internet Trends 2018, was just released. While the more than 290 slides in the full report come packed with useful information for driving your company forward, here are 12 important and actionable insights for business executives.