From VC To PayPal: An Inside Look at Two Chief of Staff Roles (with Anthony Rotolo)
Anthony Rotolo talks with David Nebinski about how he broke into the Chief of Staff world, first at a small African tech VC and then as a Chief of Staff at PayPal. You will also learn about earning trust, knowing when to make decisions for your leader (and when not to), and using AI to work smarter along the way.
Connect with Anthony on LinkedIn here!
Episode notes
0:01: Anthony’s background & early career
0:05: His initial move into VC and why
0:12: How he started as a data analyst and operational backbone in VC
0:18: His natural shift into a Chief of Staff role at the VC
0:26: Joining PayPal as an interim Chief of Staff
0:31: His post-interim CoS role at PayPal
0:33: Zooming in vs. zooming out in the role
0:36: How to be valuable without being the expert
0:41: Relationship-building and relationship-dynamics with a Principal
0:44: Advice for Chiefs of Staff on decision-making
Connect with Anthony on LinkedIn!
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