How do you stand out when your feature list looks like everyone else's? In this episode, Jonathan Leaf, CRO of BambooHR, joins host Kyle Norton (CRO at Owner.com) to break down how he's built competitive edge in undifferentiated markets—from Softchoice to AWS, RingCentral, and now BambooHR.
Jonathan shares how to:
- Win when products look the same
- Stay maniacally focused on a specific segment and ICP
- Use values and leader visibility to drive accountability and performance
- Build organizational rhythm that fuels execution
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Chapters:
00:00 Introducing Jonathan Leaf, CRO of BambooHR
01:06 Career Journey: From SoftChoice to AWS to BambooHR
03:14 Inside BambooHR: Scale, Customers, and Focus Areas
04:35 Defining SoftChoice and Competing Without IP
06:25 Competing in Crowded, Undifferentiated Markets
09:37 Building Differentiation Through Mission, Focus, and People
11:39 How Culture and Customer Experience Win Deals
17:02 Being Prescriptive: Focusing on the Right Market Segment
21:42 Hiring for Mission Alignment and Go-to-Market Evolution
26:38 Testing and Validating Sales Profiles with Data and AI
29:47 Inspecting Strategy and Operating Cadence for New Growth Bets
39:12 Why Execution and Focus Win in Competitive Markets
40:09 Positioning Products Beyond Features and Selling Peace of Mind
43:15 Point-of-View Positioning and Radical Transparency in Sales
47:19 When the Sales Experience Reflects Customer Experience
49:29 Culture as a Revenue Driver and Operationalizing Company Values
57:55 Maintaining Culture During Change and Leading with Visibility
03:52 Building Alignment and Empowerment Across the Executive Team
12:26 Lessons in Career Patience, Growth, and Self-Balance
13:42 Quickfire: Leadership, Learning, and Hard-Earned Lessons
