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.

—

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

—

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

—

Where to find Alyssa Henry:

• LinkedIn: https://linkedin.com/in/alyssa-henry-0905692
• Twitter/X: https://twitter.com/alyssahhenry

—

Where to find Brett Berson:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

—

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

—

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