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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.
Your Legacy, Amplified: Preparing the Business for Growth Without You at the Helm
Wed, Jun 25, 2025 — Every founder I’ve ever met pours themselves into their businesses—every decision, every milestone, every customer won (or lost) feels personal. And rightfully so. For many, the company isn't just a source of income; it's the embodiment of years of grit, sacrifice, and belief. But here’s the hard truth: what helped a company grow in its early years often isn’t what’s needed to scale. At some point, the business becomes bigger than one person—even the founder. That moment doesn't have to feel like an ending. In fact, it’s the beginning of something powerful.
From Concept to Execution: A Step-by-Step CEO Playbook for Go-to-Market Success, Part One
Mon, Jun 23, 2025 — Every CEO knows this nightmare scenario: Your team spent months crafting the "perfect" go-to-market strategy, only to watch it crumble during execution. Resources hemorrhage, timelines slip, and while you're still troubleshooting internal alignment issues, competitors are capturing the market opportunity you identified first.
AI Isn’t a Replacement—It’s an Accelerator: How SMBs Can Use AI to Elevate Human Performance Across the Organization
Fri, Jun 20, 2025 — We’re in the midst of a generational shift—one where artificial intelligence is reshaping how we work, how we serve customers, and how we think about the roles of humans in business. But here’s the reality I’ve seen across dozens of companies: AI is not a silver bullet, and it’s not a pink slip. It’s a power tool—one that requires a skilled operator, a clear use case, and the right safety measures in place.
Navigating Economic Waves: Charting a Course for Business Growth in 2025 and Beyond
Wed, Jun 18, 2025 — In today's rapidly changing business landscape, success isn't about surviving—it's about strategically thriving. As a seasoned executive and growth strategist, I've learned that understanding economic trends isn't just an academic exercise; it's the difference between being a market leader and a market follower.
Winning the Fraud and Cybersecurity Race: A Go-to-Market Blueprint for Competitive Edge
Thu, Jun 5, 2025 — Fraud and cybercrime have become a systemic, trillion-dollar drag on the global economy—but the fight to turn the curve is more than a market opportunity. Over the past few years, I have worked alongside cybersecurity and fraud-management teams in government, banking, and payments, and nothing is more satisfying than seeing a new solution stop a romance scam or prevent a pensioner from losing their life savings.
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.
Tariffs and Your Next Chapter | From Cost Burden to Market Edge: Turning Tariffs into a Competitive Advantage
Fri, Apr 11, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
Tariffs and Your Next Chapter | The 5 Biggest Mistakes Leaders Make Around Tariffs
Thu, Apr 10, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
From Crisis to Competitive Edge: Leveraging Digital Transformation in Tough Economic Times
Wed, Apr 9, 2025 — In today's unpredictable economic climate, small and medium-sized business (SMB) owners face numerous challenges, including fluctuating market conditions, supply chain disruptions, and evolving consumer behaviors. These uncertainties can be daunting for business leaders striving to maintain stability and growth. However, by reframing economic downturns as opportunities for transformation, SMBs can leverage digital technologies to not only survive but thrive amid these challenges.