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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.
What Can Chester Cheetah Tell You About Your Brand?
Fri, Jul 18, 2025 — Imagine an argument about whether Chester – yes, Chester of Cheetos fame – should be 2D or 3D. The debate raged in almost every corner of Frito-Lay headquarters at the time. There were strong opinions on both sides and an even more provocative discussion about the brand’s target audience. At the time, two of every three bags of Cheetos purchased were consumed by adults, not tweens and teens. So, the debate was fair, if inconvenient.
Why CEOs Must Be Active on Social Media: Building Trust and Authenticity with Customers
Wed, May 14, 2025 — I’ve seen firsthand how a CEO’s presence on social media changes how people view a company. Customers, employees, and potential hires want to know who’s steering the ship. When I show up online and share my perspective, the conversations become more genuine, and trust starts to build. It’s not about self-promotion – it’s about showing the real person behind the title.
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.
Respected Boss? Trusted Coach? Why Sales Managers Need to Be Both
Mon, Apr 7, 2025 — As a front-line sales manager, distinguishing leadership from management responsibilities is critical to a sales team’s culture and success. Distinguishing between the two helps managers be more intentional about developing these very different skill sets. Sales leadership focuses on inspiring and developing people, while sales management concentrates on processes and immediate results. Effective sales professionals must balance both roles.
Sales Terraformance: A Scientific Approach to Sales Growth
Fri, Mar 28, 2025 — Most companies deploy a sales “force.” Too often, this means a bunch of people do things with good intentions, but their combined efforts do not meet company growth expectations. Most CEOs and Founders would like a better salesforce but struggle with how to impact the “art and science” of sales improvement. At Chief Outsiders, we believe more science can help uncover and develop the insights, strategies, and execution required to achieve breakthrough performance.
Drive Revenue With B2B Sales Consulting
Mon, Mar 3, 2025 — Growth doesn't happen simply by chance. It's engineered by insight, strategy, and execution, especially in complex B2B environments where longer sales cycles, shifting buyer expectations, and pressure to prove return on investment (ROI) dominate the landscape. That's where B2B sales consulting becomes a revenue accelerator, not a luxury.
Tech Stacks: Transforming Your Business in the Digital Age
Mon, Jan 6, 2025 — In today's hyper-connected business world, technology isn't just a tool—it's the difference between thriving and merely surviving. The digital landscape has transformed how companies approach sales and marketing, making a strategic technology stack more critical than ever.
Digital Marketing Mastery: A CEO's Roadmap to Competitive Advantage
Thu, Oct 17, 2024 — In today's digital-driven business landscape, CEOs can no longer afford to take a hands-off approach to their company's marketing efforts. With over 80% of the modern buyer's journey happening online, a solid digital marketing strategy has become critical for driving growth and staying competitive.
Maximizing Returns with AI-Enabled Selling – A Strategic Blueprint
Mon, Oct 14, 2024 — In the first two blogs of this three-part series, we introduced the concept of AI-enabled selling, the need for an integrated strategy, and a framework for mapping the myriad technologies available to the needs of the sales organization. We learned that the adoption of AI-enabled selling—the sophisticated merger of AI technologies with traditional sales processes—has become instrumental in transforming organizational sales approaches. With this foundation in place, we are in a better position to discuss the payback and chart a path forward that aligns with a company’s highest priorities.