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Does Your Contracting Pipeline Live in the Owner’s Head?
Relationships matter in construction, and most subcontractors have good ones. The owner or president carries the key customer relationships, and the project managers carry everything else. That arrangement can work well. It is also fragile. In our last post, we asked whether you know by name who owns each strategic account. This one looks at what happens when the answer is the owner.
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.
When Customer Value Becomes the Growth Engine
Sun, Sep 13, 2026 — Executive Takeaways Customer value drives growth when insight turns into actions that advance customer priorities. Strong relationships begin with understanding the pressures and outcomes that matter most to CXOs. Growth comes from converting insights into new ideas, and relevant solutions, achieving measurable impact. ABM aligns sales and marketing teams around high-value accounts to build deeper, more strategic and enduring relationships. This blog is part of Chief Outsiders’ New Growth Imperative series, designed to help CEOs and leadership teams engage executive decision-makers at targeted strategic accounts by turning deep insights into compelling customer value.
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.
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.
The Evolution of B2B Selling: Focus on Helping Customers Buy
Thu, Jan 15, 2026 — Many B2B companies are experiencing longer sales cycles, declining win rates, and increasingly unreliable forecasts—not because their sales teams are ineffective, but because their customers are struggling to buy. Executive Takeaways B2B buyers face overwhelming complexity, not a lack of information. Long sales cycles and no-decisions often reflect buyer indecision, not sales failure. Winning sellers focus on boosting buyer confidence, not pitching products. Helping customers buy is now the key to competitive differentiation.