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Your CRM Is Already Telling You Where the Revenue Is. Are You Listening?
Most SMBs don't have a data problem. They have a listening problem.
Between CRM records, transaction history, and years of customer activity, most companies are sitting on far more information than they're actually using. The data isn't missing. It's just too much, too scattered, and too slow to work through manually for anyone to reliably act on it.
The Contrarian Brand Play: Why Right Now Is the Best Time to Invest in Brand
Fri, Sep 18, 2026 — Executive Takeaways Most companies are cutting brand spend to fund rising paid acquisition costs. That is the wrong response. Brand awareness now drives AI citations, and AI citations drive Day One shortlist inclusion. Google's redesign of Search makes brand recognition more important; AI systems favor brands users already know. The companies investing in brand while competitors pull back are building advantages at lower cost. Part 4 of our four-part series on the evolving AI search landscape and what B2B leaders need to know to stay competitive.
Stop Buying AI Tools. Start Asking This Question First.
Fri, Sep 18, 2026 — Most CEOs start their AI planning in the wrong place. They start with a tool. A demo catches their eye, a peer recommends a platform, or a vendor makes a compelling pitch, and suddenly the conversation is about which AI product to buy instead of what the business actually needs it to do.
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.
Your Buyers Have Already Shortlisted You—Or They Haven't
Wed, Sep 2, 2026 — Executive Takeaways 95% of B2B buyers purchase from the vendors on their initial shortlist, formed before any formal buying process begins. That shortlist is increasingly built inside AI platforms your analytics can't see. AI referral traffic is roughly 1% of total website traffic, yet 15% or more of conversions appear to originate from AI-influenced research, a gap standard attribution misses entirely. If you're not on the Day One list, spend alone won't fix it. Part 3 of our four-part series on the evolving AI search landscape and what B2B leaders need to know to stay competitive.
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 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.
The Gap Between AI Output and Real Marketing Leadership, Part 2
Fri, Aug 14, 2026 — Executive Takeaways AI reasons from the past. Vision requires betting on what hasn't happened yet. A generic answer that sounds smart is still generic. The right questions expose the gap between AI output and executive judgment. Fractional leadership fills the judgment gap AI can't close.
Marketing's Lost Generation: Why Execution Outpaced Strategy
Fri, Aug 14, 2026 — Executive Takeaways Mid-career marketers mastered execution before strategy, and the gap shows at the leadership level. Without strategic clarity, marketing activity becomes noise instead of advantage. Marketing's complexity gets masked by opinions, and only the CEO can establish the conditions to fix it. The solution isn't more campaigns. It's strategic capability paired with execution power. This blog is part of Chief Outsiders’ Marketing Leadership for CEOs series, an ongoing examination of the critical dimensions of Marketing (the capital “M” is intentional, as you’ll see) that every CEO needs to understand.