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.
Find me on:

Recent Posts

Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI

Outsider Insights | You Can't Measure AI ROI If You Can't Measure Marketing ROI

Tue, Apr 28, 2026 | Posted by Dawn Werry

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.

Read More