Growth Insights for CEOs

Outsider Insights | The Backup Plan You Don't Have Is Already Costing You
Executive Takeaways
- Commercial team gaps happen for many reasons: someone leaves, someone is underperforming, or the business needs a capability the current team doesn’t have.
- Mid-sized companies tend to run lean, which means there’s rarely a qualified backup ready to step into a critical role.
- The real cost of that gap isn’t the empty seat. Priorities slow, teams lose direction, good people get frustrated, and commercial efforts stall.
- Rushing a permanent hire isn’t always the answer. Fractional resources can keep the business moving while you make the right long-term decision.
- The best time to decide how you’ll handle a critical commercial is before one opens.
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

When to Hire a Fractional CMO vs Full-Time CMO
Tue, May 26, 2026 — Executive Takeaways The distinction between fractional and full-time CMO isn't hours or cost — it's orientation and incentives. Fractional wins in definable contexts: transitions, growth stages, and moments requiring an honest broker. The CEO-CMO trust gap is structural, not personal. Fractional leadership changes the architecture. Full-time is right for large-scale transformation. CEOs must match the model to the moment.

Should I Hire a Fractional CMO?
Fri, May 8, 2026 — Executive Takeaways A full-time CMO can cost $1M in year one — before the first campaign ships. Full-time CMOs optimize for tenure. Fractional CMOs optimize for outcomes. Fractional CMOs bring cross-industry pattern recognition that deepens with every engagement. Fractional leadership wins in specific, definable contexts. The next article maps exactly when.
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Outsider Insights | Agentic AI: What CEOs Need to Know Before They Invest
Wed, Feb 18, 2026 — 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. Executive Takeaways Gen AI assists. Agentic AI acts, and requires a higher level of organizational readiness. AI-driven buyer research is reshaping vendor visibility before sales engagement begins. Agentic AI initiatives fail when layered onto unclear processes, weak data, or undefined business problems. Operational discipline, not technology adoption, determines whether AI becomes a scalable growth lever.
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The Evolution of B2B Selling: Focus on Helping Customers Buy
Thu, Jan 15, 2026 — Many B2B companies are experiencing longer sales cycles, declining win rates, and increasingly unreliable forecasts—not because their sales teams are ineffective, but because their customers are struggling to buy. Executive Takeaways B2B buyers face overwhelming complexity, not a lack of information. Long sales cycles and no-decisions often reflect buyer indecision, not sales failure. Winning sellers focus on boosting buyer confidence, not pitching products. Helping customers buy is now the key to competitive differentiation.

Outsider Insights | Beyond the Sale—Why CEOs Are Turning Attention to Retention and Expansion
Wed, Jan 14, 2026 — 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.

Outsider Insights | What We Learned Helping CEOs Grow in 2025
Mon, Jan 5, 2026 — 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.

Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
Mon, Nov 3, 2025 — 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.

Go Time? Or Just Another Head Fake? How Mid-Market CEOs Should Move Forward Now
Wed, Jun 25, 2025 — Six months ago, we diagnosed a condition gripping mid-market companies across the country: Waitflation. Leaders were holding back—not because of financial hardship, but because of economic ambiguity. Interest rates were high, forecasts were fuzzy, and confidence was low. The result? A national game of “wait and see.” Now, as we enter a volatile summer, it’s time to ask: Is it go time?

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.