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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.
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.
8 Strategic Moves to Grow Your Business with AI
Wed, Jun 18, 2025 — Top takeaways and action items from Mary Meeker’s 2025 AI Trends Report Generative AI is accelerating at a pace we've never seen before. ChatGPT, for example, reached 800 million users in just 17 months—far faster than the 11 years it took Google Search to hit similar annual query volumes. Tech giants are pouring hundreds of billions into AI infrastructure, making these tools cheaper, faster, and more accessible than ever before.
From Market Competitor to Trusted Advisor: Leveraging Research to Dominate Your ABM Strategy
Thu, Jun 12, 2025 — My previous article explored how research-based thought leadership transforms prospect relationships in ABM programs. Now, let's tackle the practical framework: How do you build and implement research-driven ABM to elevate yourself from being seen as just another market competitor to becoming an indispensable trusted advisor?
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.
The Secret Weapon in ABM: How Research-Based Thought Leadership Transforms Prospect Relationships
Tue, Jun 3, 2025 — ABM programs that consistently outperform are those anchored in credible, research-based thought leadership. I've seen it repeatedly throughout my career as a marketing leader. In my experience, this approach leads to improved conversion from the first meeting to the next sales stages and shorter sales cycles. The secret isn't just better targeting – it's the authority established through proprietary insights.
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.
Growth Hurts. Let it.
Wed, May 14, 2025 — “Don’t Risk Too Little. Don’t Rescue Too Soon” – the growth lesson I learned outside the boardroom. My son once played striker in a school tournament. With minutes left and his team trailing, he broke through the defense and had a clean look at the goal. He hesitated, and the shot went wide.