Business Growth Strategies For CEOs: Top CMOs On Marketing Strategy Implementations

John Blessing

As the Chief Outsiders Chief Sales Program Manager and CSO, John is an accomplished leader who consistently builds success in growth and turnaround situations in a variety of industries, including professional and financial services, retail, and SaaS. He turns around poor performance and accelerates growth by building and executing strategic sales programs. He also drives sales and operations alignment to deliver breakthrough revenue. With experience in several industries, John offers perspectives not hindered by industry-specific paradigms.

Outsider Insights | The Backup Plan You Don't Have Is Already Costing You

Fri, Aug 21, 2026 | Posted by Dawn Werry

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.

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Growth Insights for CEOs