Karen Hayward

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Karen Hayward is a Managing Partner and CMO of Chief Outsiders. Karen is a results-oriented marketing, sales and operations executive with a proven track record for building and executing strategic programs that accelerate revenue. Karen’s industry marketing awards include a DemandGen Top 10 Award for "Using Sales and Marketing Automation to Fuel Corporate Growth" (2008 - CenterBeam) and a Stevie Finalist recognition for "Best Marketing Department" from the American Business Awards. In 2004, Karen was named a “Selling All-Star” by Selling (a monthly publication of Institutional Investor. She has also been a featured speaker at Interop 2007, On24 Webcast on Lead Farming, and a guest lecturer at USC East Bay. In 2010, Karen was recognized by CRN as one of the "Power 100: The Most Powerful Women of the Channel" for driving top-line revenue growth and revving up CenterBeam's social media program. Karen holds a Bachelor of Commerce degree from Concordia University in Montreal, Quebec, Canada.
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Recent Posts

Growth Without Guesswork: The Questions Great Vistage Chairs Ask

Growth Without Guesswork: The Questions Great Vistage Chairs Ask

Fri, May 15, 2026 | Posted by Karen Hayward

Executive Takeaways

  • Most CEOs are managing growth on assumptions that no longer reflect how buyers actually buy.
  • The best Chair question isn't "how is sales going?" It's "where are the growth leaks?"
  • AI search is already a revenue issue, not a future one.
  • Insight without commitment is just a good conversation.

After leading more than 150 Vistage workshops, working with hundreds of CEOs navigating growth challenges, and spending more than 10 years as a Vistage member myself, I’ve noticed a consistent pattern in conversations with business leaders. No matter the industry, the symptoms sound familiar.

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