Growth Insights for CEOs

Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI
Executive Takeaways
- Most mid-market companies lack the measurement foundation to evaluate AI — or any marketing investment.
- Hours saved, speed to market, and revenue realized are the three key AI ROI markers — baseline required.
- AI amplifies what's working. If measurement is broken, AI won't fix it.
- Real results start with a defined problem and a way to measure it — not the tool.
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.
Recent Posts

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.

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.

Tariffs and Your Next Chapter: Turning Disruption into Go-to-Market Growth
Mon, Apr 7, 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.
Stay up-to-date with the latest from Chief Outsiders

Leveraging AI: Is Your Company Future-Ready? | A Roadmap of Eight Essential AI Steps for Success
Mon, Mar 24, 2025 — A BCGX study reveals just 6% of companies have trained 25%+ of their workforce on Gen AI tools, yet 100% will require upskilling within two years. With Accenture projecting AI will augment 40% of work hours and McKinsey forecasting 70% automation of business activities by 2030, the urgency for strategic AI adoption has never been greater.

The AI Revolution: Why SaaS Companies Must Adapt or Become Obsolete
Fri, Mar 7, 2025 — In 2025, AI agents are revolutionizing the SaaS industry, transforming traditional cloud-based applications into dynamic, self-optimizing platforms. For business leaders, this trend represents a seismic shift from FOMO (Fear of Missing Out) to FOBO (Fear of Becoming Obsolete), with the rapid pace of AI adoption and its transformative potential driving noticeable shifts in strategy.

How to Use Positioning to Own Your Market
Wed, Feb 26, 2025 — Become a big fish in your pond Of all the marketing strategy lessons we at Chief Outsiders share with founders and business leaders, positioning ranks among the most critical. It truly is a difference-maker for businesses that wish to become the leader of the pack—to become, in fishing parlance, the big fish in your pond.

Unlocking Business Growth: The Power of USP, Value Proposition, and Positioning
Wed, Jan 15, 2025 — As a CEO, you understand that growth depends on effectively communicating the value of your products and services to your customers. However, our language and strategies to convey that value can often get muddled. That’s where understanding key concepts like Unique Selling Proposition (USP), Value Proposition, and Positioning becomes crucial to driving brand differentiation and customer loyalty. In this post, I’ll break down the differences between these terms and explain how they contribute to the growth of your business.

A Strategic Guide to Double-Digit Revenue Growth
Tue, Jan 14, 2025 — CEOs face intense pressures today to deliver consistent double-digit revenue growth year after year. But with the right strategy focused on business development, sales, and key performance indicators - hitting that 10% annual growth benchmark is achievable. This article provides a blueprint for leaders looking to spur growth. As a result of the current market conditions, a new benchmark has been established: If your company can't show a minimum Compound Annual Growth Rate of 10 percent, you are putting yourself and your company at risk. As never before, revenue growth is the key to a business's health, high corporate valuations – and CEO job security.

Eight Steps to Increase Revenue from Your Existing Customers
Wed, Dec 11, 2024 — There are two ways to grow your business. The first is by acquiring new customers. The second is retaining your current customers and increasing their ongoing revenue stream. Many companies focus their strategic marketing initiatives on finding new markets, new customers, and new applications for their current product offerings. While this focus is essential, many companies lose sight of their best growth opportunities … their current customers. Current customers allow you to grow your revenue without the increased costs associated with new client acquisition activities.