Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert.

In today’s episode we discuss:

• The principles of effective org design
• Signs your company needs a re-org
• Square’s GM-led org design, and the reasoning behind it
• Lessons on incentive-design, pricing, planning, and decision-making at scale
• The step-by-step process behind a recent re-org at Square
• 5 lessons from Alyssa Henry, CEO at Square

Referenced:

Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692

Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd

Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9

Square: https://squareup.com/gb/en

Where to find Saumil Mehta:

Twitter: https://twitter.com/saumil

Linkedin: https://www.linkedin.com/in/saumilmehta1/

Blog: https://medium.com/@saumil

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

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

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

[00:02:22] Intro

[00:04:20] The principles of effective org design

[00:04:32] #1 Align on goals

[00:06:14] #2 Separate design considerations from human considerations

[00:08:03] #3 Define clear reasons each team exists

[00:09:21] #4 Design for durability

[00:09:49] #5 Be very intentional with comms

[00:10:14] Some stories behind the principles

[00:13:55] How to know when you need a re-org

[00:16:14] Managing inevitable tradeoffs in org design

[00:20:45] Square's "GM-led" structure

[00:23:05] Why Square centralized GTM

[00:25:39] Managing pricing and packaging across a complex org

[00:29:28] Examples of Square's written principles

[00:31:19] How Square determines what each GM owns

[00:38:35] Collaboration across GMs and products

[00:40:32] Key lessons on planning and decision-making at scale

[00:43:15] Designing incentives across a massive org

[00:49:03] Two reasons GM structures go wrong

[00:52:03] 6 Step re-org walkthrough

[00:52:37] Step 1: Triggering the re-org

[00:53:59] Step 2: Sketching a proposed org design

[00:56:17] Step 3: Checking against key criteria

[00:59:22] Step 4: Finalizing approach with leadership

[01:00:04] Step 5: Planning comms

[01:01:58] Step 6: Executing comms

[01:04:20] Signals a re-org worked vs failed

[01:07:13] 5 lessons from Alyssa Henry, CEO at Square