Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent.

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In today’s episode, we discuss:

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Referenced:

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Where to find Alyssa Henry:

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:20) Lessons from Microsoft and Amazon

(08:29) Noticeable consistencies in the human condition

(10:50) Differences in culture at Amazon, Microsoft and Square

(13:27) Why “customers come first,” even above employees and community

(14:01) Why fast-followers can be less customer-focused

(15:50) The challenge of commercializing research projects

(18:58) Joining Square and “building a picture” of the org

(24:55) Knowing what to replicate from past companies

(27:45) Questioning norms in new companies

(28:41) The importance of effective communication systems

(31:31) How to operationalize company values

(33:38) Why shared beliefs are crucial for good company culture

(37:05) Building Minimal Remarkable Products at Square

(38:13) How to scale an aesthetic

(42:46) Org design lessons from Square

(50:06) How to align different teams behind business priorities

(52:57) Lessons learned from fierce competition

(57:39) The “fast follower” vs “pioneer” playbook

(61:05) The original thinking behind AWS

(66:08) The unlikely origin of Amazon CloudFront and other products

(73:47) How Jeff Bezos influenced Alyssa