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