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

Pipeline Integrity: How Hidden Revenue Leaks Sabotage Growth

Pipeline Integrity: How Hidden Revenue Leaks Sabotage Growth

Tue, Apr 7, 2026 | Posted by The Chief Outsider

Executive Takeaways

A pipeline that looks healthy can still be losing 15–25% of achievable revenue.
When teams define MQLs, SQLs, and pipeline stages differently, every other fix fails.
Work backwards from your revenue target using conversion rates to find and close the gaps.
A one-time diagnostic fades without the right recurring reviews and accountability rhythms.

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