Moving Pega to Cloud: paced transition

Ken recounts Pega's cautious cloud migration, sequencing sales, product and customer readiness to ensure sustainability.

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In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.

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LINKS:

Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/

Pegasystems: https://www.pega.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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