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Jonathan Leaf
CRO at BambooHR with prior leadership roles at Softchoice, AWS, and RingCentral; focuses on winning in crowded markets through mission-driven strategy, culture, and execution.
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Nov 5, 2025
• 1h 19min
E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)
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Jonathan Leaf, CRO at BambooHR, shares insights from his impressive journey through Softchoice, AWS, and RingCentral. He discusses how to thrive in crowded markets by honing in on specific customer segments and leveraging mission-driven culture. Leaf emphasizes the importance of trust and customer experience in winning deals and outlines how BambooHR focuses on SMBs to drive growth. He also highlights the role of visibility and values in building accountability, urging leaders to align their teams with clear goals for maximum impact.
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