Karen Hayward

Picture of Karen Hayward
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

From Plateau to Acceleration: A PE Playbook for Unlocking Predictable Financial Growth

From Plateau to Acceleration: A PE Playbook for Unlocking Predictable Financial Growth

Jul 7, 2025 2:51:24 PM | Posted by Craig Levinsohn

In a recent episode of Dream and Soar with Chuck and Friends, Chuck sat down with Craig Levinsohn, Chief Strategy & Revenue Officer at Chief Outsiders, to unpack one of the most pressing questions in private equity today:

“How can portfolio companies achieve their next phase of growth—and do it predictably, consistently, at scale, and profitably?”

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