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Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt
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 | Google Just Declared the Search Box Dead: What CEOs Need to Know
Mon, Jun 15, 2026 — Executive Takeaways Google just redesigned Search for the first time in 25 years. 94% of B2B buyers use AI to research vendors before your sales team knows they exist. The companies earning AI citations share one thing: content written to inform, not to sell. 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 Is Already Improving B2B Sales Performance. Here’s the Framework to Make It Work for You
Wed, Jun 10, 2026 — Executive Takeaways AI is already delivering measurable results in B2B sales — this is not hype. Mapping AI capabilities to your prioritized sales performance challenges is the right place to start. Achieving significant ROI requires a diagnosis of your current sales environment, a pilot with defined success metrics, and a plan for deployment and scale. The window to establish a competitive advantage in sales by using AI is open — but not indefinitely.
Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI
Tue, Apr 28, 2026 — Executive Takeaways Most mid-market companies lack the measurement foundation to evaluate AI — or any marketing investment. Hours saved, speed to market, and revenue realized are the three key AI ROI markers — baseline required. AI amplifies what's working. If measurement is broken, AI won't fix it. Real results start with a defined problem and a way to measure it — not the tool. 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.
The AI Training Economy: The Human Expertise Behind the Agent Revolution
Wed, Apr 22, 2026 — The challenge of training AI models on human expertise is not new. What is new is that three college dropouts just built a $10 billion business by productizing that exact problem at scale. Executive Takeaways The AI training economy is already here — and a $10 billion startup is proof. You can't have capable AI agents without well-trained models. Human expertise isn't being replaced; it's being harvested. Fast followers still have a window, but waiting another 18 months may mean competing on scale alone, not quality. Most organizations are underestimating the speed of this workforce transformation. The time to build AI fluency is now.
Why MedTech’s Brilliant Innovators Must Also Become Commercial Architects
Thu, Mar 26, 2026 — Great technology is necessary. It is not sufficient. The graveyard of MedTech is lined with brilliant innovations that never found their market — not because of scientific failure, but commercial invisibility. I just returned from LSI USA ‘26 in Dana Point — the most impressive gathering of emerging MedTech talent I’ve witnessed in decades. The event convened 2,000 executives, 394 presenting startups, and over 500 active investors and strategics. The scientific ambition in that room was extraordinary.
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.
AI Strategy for Financial Services CEOs: Why “Good Enough” is no Longer Enough
Mon, Feb 23, 2026 — AI in financial services has moved from lofty claims about AI's use to being at the center of the growth conversation, shaping how you compete, run, and stay trusted. Margins are under pressure as customers benchmark you against their best digital experiences, whether they are opening a checking account, redeeming loyalty points, disputing a card charge, or seeking hardship help.
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Outsider Insights | Agentic AI: What CEOs Need to Know Before They Invest
Wed, Feb 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 Gen AI assists. Agentic AI acts, and requires a higher level of organizational readiness. AI-driven buyer research is reshaping vendor visibility before sales engagement begins. Agentic AI initiatives fail when layered onto unclear processes, weak data, or undefined business problems. Operational discipline, not technology adoption, determines whether AI becomes a scalable growth lever.
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.