Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft‪)‬ In Depth

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:

Lessons from Amazon, Microsoft, and Square

“Minimum Remarkable Products” versus Minimum Viable Products

Navigating different work cultures in big tech

Insider reactions to the disruptive launch of AWS

“Pioneer” versus “fast-follower” companies

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Referenced:

Amazon: https://www.amazon.com


Amazon Web Services: https://aws.amazon.com


Bill Gates: https://www.linkedin.com/in/williamhgates


Block, Inc: https://block.xyz


Cash App: https://cash.app


Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one


Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1


Jack Dorsey: https://twitter.com/Jack


James Hamilton: https://www.linkedin.com/in/jameshamilton4


Jeff Bezos: https://twitter.com/jeffbezos


Microsoft: https://www.microsoft.com


Oracle Corporation: https://www.oracle.com


Sarah Friar: https://www.linkedin.com/in/sarah-friar


Square: https://squareup.com


Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817


WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424


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Where to find Alyssa Henry:

LinkedIn: https://linkedin.com/in/alyssa-henry-0905692


Twitter/X: https://twitter.com/alyssahhenry


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Where to find Brett Berson:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Twitter/X: https://twitter.com/brettberson


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Where to find First Round Capital:

Website: https://firstround.com/


First Round Review: https://review.firstround.com/


Twitter: https://twitter.com/firstround


YouTube: https://www.youtube.com/@FirstRoundCapital


This podcast on all platforms: https://review.firstround.com/podcast


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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