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Outsider Insights | You Built Something Different. Your Messaging Made It Sound the Same.
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 | Two Accounts are Quietly Running Your Business
Thu, Sep 17, 2026 — Executive Takeaways If more than 40% of your revenue comes from a handful of accounts, a meaningful share of your company’s revenue is sitting outside your control. Your revenue growth may look healthy, but it’s at risk. Concentration risks go beyond losing a big account. It changes the leverage in every conversation you have with that customer. One key cause of concentration risk is the lack of a systematic way to bring in new logos. As a result, company growth comes mainly from current account expansion and a few salespeople. Companies need a balance of both. Diagnosing your risk is a simple exercise that you can do in a few minutes this week. 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 | The Backup Plan You Don't Have Is Already Costing You
Fri, Aug 21, 2026 — Executive Takeaways Commercial team gaps happen for many reasons: someone leaves, someone is underperforming, or the business needs a capability the current team doesn’t have. Mid-sized companies tend to run lean, which means there’s rarely a qualified backup ready to step into a critical role. The real cost of that gap isn’t the empty seat. Priorities slow, teams lose direction, good people get frustrated, and commercial efforts stall. Rushing a permanent hire isn’t always the answer. Fractional resources can keep the business moving while you make the right long-term decision. The best time to decide how you’ll handle a critical commercial is before one opens. 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 Four Mistakes Founder-Led Companies Make Building a Revenue Organization
Tue, Aug 11, 2026 — Executive Takeaways The commercial function that got you to $10M–$15M was built for that stage. It doesn't automatically scale to the next one. Most founders don't see the gap from the inside. Buyers will see it immediately. Seven diagnostic signals reveal whether your revenue engine is built to scale — or just built for today. The earlier you find the gaps, the easier they are to close.
Are You Building a Business That's Ready to Scale - or Just a Business That Has Had Great Growth?
Mon, Jul 27, 2026 — Executive Takeaways The commercial function that got you to $10M–$15M was built for that stage. It doesn't automatically scale to the next one. Most founders don't see the gap from the inside. Buyers will see it immediately. Seven diagnostic signals reveal whether your revenue engine is built to scale — or just built for today. The earlier you find the gaps, the less expensive they are to close. There is a version of business success that feels like momentum but isn't quite there yet.
Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt
Fri, Jul 24, 2026 — Executive Takeaways Sales reps focus on what they're paid and measured on, even if that strays from business strategy and goals. Many compensation plans and account structures quietly reward protecting revenue, not creating it. Adding a quota target without changing the underlying structure just adds pressure, not pipeline. Fixing this starts with the comp plan and account map, not a pep talk about hustle. 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.
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.
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.
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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.