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Uncertainty Is Real. Opportunity Is Too.
The headlines say one thing. The data says something more nuanced. Here's what mid-market CEOs should actually be paying attention to right now. This two-part series from Chief Outsiders Founder & CEO Art Saxby explores what the data actually shows about CEO confidence, why this moment is different from past disruptions, and where mid-market companies are finding real growth opportunities right now.
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 CEO's Role as Champion of the Unified GTM Operating Model
Tue, May 26, 2026 — Executive Takeaways The CEO must be the architect and champion of the GTM model — not its operator. Only the CEO has the cross-functional authority to make a unified GTM model stick. If the model only works when you're in the room, it's not a system. When it's working, your calendar proves it.
Stop Hosting Alignment Meetings and Start Building a Unified GTM Operating Model
Wed, May 6, 2026 — Executive Takeaways You can't meeting your way out of a system design problem. Alignment meetings are reactive, CEO-dependent, and fix symptoms — not root causes. A unified GTM Operating Model creates alignment by design, not by force. When the system works, the CEO stops mediating and starts leading.
Marketing Leadership for CEOs: An Executive Guide to Growth
Mon, May 4, 2026 — Executive Takeaways At a certain scale, Marketing stops being a support function and becomes the company's growth system. Everyone has opinions about marketing, which means it rarely gets the disciplined oversight it actually requires. The CEO is uniquely positioned to set clear intent and hold the function accountable. As a connected system, Marketing drives alignment and focus. 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.
How to Develop Future C-Suite Leaders: A Guide for Mentoring and Succession Planning
Fri, Apr 10, 2026 — Executive Takeaways Succession gaps quietly erode growth, value, and decision speed Strong companies treat succession as a continuous leadership discipline A 1/3/5-year talent map builds a visible, scalable leadership pipeline Sponsorship, mentoring, and coaching turn high-potential talent into ready leaders Ambition is the easy part. The real question is whether your company’s future CEO’s, CFOs, COOs, CMO’s and CROs are already growing inside the business long before you need them.
Pipeline Integrity: How Hidden Revenue Leaks Sabotage Growth
Tue, Apr 7, 2026 — Executive Takeaways A pipeline that looks healthy can still be losing 15–25% of achievable revenue. When teams define MQLs, SQLs, and pipeline stages differently, every other fix fails. Work backwards from your revenue target using conversion rates to find and close the gaps. A one-time diagnostic fades without the right recurring reviews and accountability rhythms.
CPG Industry: Is Now the Time to Start Strategizing a Price Increase?
Fri, Apr 3, 2026 — The short answer is yes, and the operators who begin planning now will be the ones who stay in control of their margins. This isn't alarmism. It's a clear look at the cost-structure reality taking shape while much of the industry is still operating with a 2021–2022 mindset. Executive Takeaways Start planning a price increase now, not when you need one. Waiting until margin pressure forces your hand means you've already lost leverage. Energy and input costs are structurally elevated and not going back down. Brands still operating with a 2021–2022 mindset are walking into margin compression. Renovation and innovation are what make price increases stick. Pairing a price move with product news gives retailers a reason to support it and consumers a reason to stay.
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.
Turning Competing Revenue Team Truths into Market Insight
Tue, Mar 10, 2026 — Executive Takeaways Sales, Marketing, and Customer Success each see different parts of the market. Conflicting perspectives usually reflect incomplete insight, not poor execution. Cross-functional pipeline, win/loss, and customer data turn friction into insight. A unified GTM operating model aligns teams around shared market truth.