Bob Sherlock

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Bob Sherlock often works with companies serving business markets that face one of two challenges: · An innovative offering that isn’t ramping up sales fast enough · Getting squeezed on price Bob solves those problems by helping clients find their Hidden Value, message it so that prospects perceive that value, and pricing to get paid for it. As a result, his clients can grow sales and margins at the same time. Bob’s experience includes consulting at Marketwerks and The ProAction Group, and founding and running a venture-funded logistics service provider operating a network of automated, unmanned delivery drop points. Earlier, Sherlock was CMO for Wickes Inc., a distributor and retailer of building materials.
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Recent Posts

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

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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