Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers

Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers

March 31, 2026 · 32 min

About this episode

Rob discusses how to find and work with owner-level thinkers in a business context.

How do you find someone who thinks like an owner, not just a task-doer? In this episode, Rob digs into a batch of listener questions about task level, project level, and owner level thinkers. He covers how to identify them, what they cost, where to find them, and why building a team of exceptional people creates a virtuous cycle that lifts everyone up. Topics we cover: (4:13) – Defining task, project, and owner level thinkers (7:32) – Are owner level thinkers born or built? (10:16) – Compensation ranges for owner level thinkers (11:53) – W2 vs. contractor for senior hires (15:53) – Do you actually need owner level thinkers? (17:36) – Where to find project and owner level thinkers (20:16) – How long to integrate them into your company (24:40) – How to identify them in job interviews (29:38) – Why you won't always get hires right Links from the show: Rob Walling's Essays Rob Walling’s Newsletter Rob Walling YouTube The SaaS Playbook Remote First Recruiting MicroConf TinySeed SaaS Institute Discretion Capital If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from…

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