The Revenue Leadership Podcast with Kyle Norton E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)
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Nov 5, 2025 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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Service And Culture Can Be Your IP
- Companies without proprietary IP can still win by how they show up to customers.
- Culture, leadership visibility, and people development become the differentiators in crowded markets.
Be Maniacal About Your ICP
- Be prescriptive: define a narrow ICP and build native, opinionated product experiences for them.
- Use partnerships for adjacencies and lean hard into outcomes, not feature parity.
Sales Experience Becomes The Deciding Signal
- Buyers default to the sales experience when features blur between vendors.
- A strong sales interaction signals expected post-sale quality and reduces buyer paralysis.
