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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.
The Augmented Revenue Engine
Tue, Aug 18, 2026 — Executive Takeaways Sellers who partner with AI are 3.7x more likely to hit quota. AI doesn't replace sellers. It removes the 75% of work that isn't selling. Win rates climb 30%+ when AI improves every funnel stage, not just one. Waiting doesn't preserve the status quo. It widens the gap to AI-enabled competitors.
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.
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.
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.
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.
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.
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.
Sales Velocity Model: A Tool for Growth Engine Mechanics
Wed, May 14, 2025 — Most companies deploy a sales “force”. Too often, their combined efforts are not meeting company growth expectations. Most CEOs would like a better growth engine, a larger sales pipeline, and more sales, but they struggle with exactly how to help their sales teams. Busy CEOs combined with people and process related complexities of Sales, often results in companies not being clear on the root cause of their growth engine problems.