Growth Insights for CEOs
The Chief Outsider
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Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
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.
Recent Posts

Why You Can’t Afford to Cut Your Marketing Investment for 2024
Wed, Oct 11, 2023 — Article 1 of the 7-part series: Accelerating Growth In 2024 with Strategic Business Planning By: Scott Wright and Jack Bowen In an era dominated by rapid change and economic unpredictability, businesses often find themselves at the crossroads of making challenging decisions, especially when it comes to budgeting. One of the areas often eyed for potential cuts is marketing. But is this a wise move?

Accelerating Growth In 2024 with Strategic Business Planning
Tue, Oct 3, 2023 — Introduction: Take Action Now to Plan for Success By: Scott Wright and Jack Bowen Temperatures are dropping, leaves are changing colors, and you can almost hear the sounds of the crowd cheering at the high school homecoming game. With these and other harbingers of the calendar’s fourth quarter, you’re likely about to sharpen your pencil, corral your executive leadership – and engage in your strategic business planning process for 2024.

AI Trends for the Progressive CEO: Navigating the Transformative Landscape
Wed, Sep 6, 2023 — By: Ed Valdez and Angus Robertson It’s hard to think of another digital trend that has shaken the foundations of conventional wisdom as AI has. Though artificial intelligence has existed in some form since the 1950s, it has taken the emergence – and the related spinal shivers – of Open AI’s ChatGPT product to truly advance the conversation.
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Branding & Growth - Why They are Inseparable
Mon, Jul 31, 2023 — Your company’s brand equals your market position and value proposition. It’s your entire strategy in a single package that is as important to your customers as it is to your long-term success.

The CEO Mindset: Resolving Sales Performance Challenges | Part 5
Fri, Jul 14, 2023 — Part 5: Moving Your KPI Levers Into Alignment Managing a sales team can be a lonely job these days. Just a few years ago, the energy in a typical sales office was positively electric. The office reverberated with the sound of ringing phones, demonstrations, strategy sessions, pipeline reviews, and the clanging of the sales bell after a deal was closed.

The CEO Mindset: Resolving Sales Performance Challenges | Part 4
Mon, Jul 3, 2023 — Part 4: Is Your Sales Process Supporting Revenue Growth? At the dinner table, you tend to get immediate feedback when the recipe of the dish being served is not quite perfected. In the business world, where the steaks….er….stakes are higher, it is no less important to have a plan which appropriately combines the ingredients for world-class success.

The CEO Mindset: Resolving Sales Performance Challenges | Part 3
Fri, Jun 23, 2023 — Part 3: Technology Platforms for the Win The market for sales enablement platforms has never been more robust. As companies like yours clamor for clients, revenue, and growth, they’re showering billions on the latest technology tools to help get them there. In fact, a recent report projects that the global market for sales enablement tech will grow at a 15 percent rate over the next five years, topping $9 billion by 2028.

The CEO Mindset: Resolving Sales Performance Challenges | Part 2
Thu, Jun 15, 2023 — Part 2: Finding the Right Talent for the Game Here today, gone tomorrow: Did you know that the average tenure of a sales professional is just about a year and a half? It’s a mind-blowing statistic that is, on the surface, an indicator of the rigors of a sales role, in any market segment.

ChatGPT is a Silver Bullet (oh, the irony)
Tue, Apr 18, 2023 — I’ve wanted to write about the fallacy of a silver bullet in business for some time. Defined as “a simple and seemingly magical solution to a complicated problem,” the silver bullet – as I’ve learned in my “grinding-it-out” years in business – simply doesn’t exist.