Bob Sherlock

Picture of Bob Sherlock
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 Comp Plan Is Quietly Telling Your Sales Team Not to Hunt

Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt

Fri, Jul 24, 2026 | Posted by Dawn Werry

Executive Takeaways

  • Sales reps focus on what they're paid and measured on, even if that strays from business strategy and goals.
  • Many compensation plans and account structures quietly reward protecting revenue, not creating it.
  • Adding a quota target without changing the underlying structure just adds pressure, not pipeline.
  • Fixing this starts with the comp plan and account map, not a pep talk about hustle.

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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