Navigating Global Payroll and Expansion

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Jeremy Henrickson is Rippling’s SVP of Product, responsible for scaling their product and design team across three continents. Previously, as Chief Product Officer at Coinbase, he oversaw 10x growth of the product and engineering organization and transformed a scrappy startup into a global cryptocurrency platform with tens of millions of users. He began his career at Apple in the 1990s and holds a BS and MS in computer science from Stanford. In today’s episode, we discuss:

• Strategies for sustaining focus and momentum at scale

• The case against MVPs

• The problem with frameworks

• “Compound startups” and how this influences Rippling’s product development process

• Advice for founders wanting to move faster

• Why you don’t understand your product unless you’re “in the weeds”

• Hiring practices at Rippling and how young PMs can build fruitful careers

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Find the transcript at: https://www.lennysnewsletter.com/p/moving-fast-and-navigating-uncertainty

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Where to find Jeremy Henrickson:

• Twitter: https://twitter.com/jeremyhenricks

• LinkedIn: https://www.linkedin.com/in/jeremyhenrickson/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Jeremy’s background

(03:24) What it was like leading product teams at Coinbase during the crypto boom

(05:25) How Jeremy kept teams focused and the biggest challenges he faced at Coinbase

(07:35) Advice for going through intense periods at work

(08:52) Maintaining velocity at scale

(12:07) An example of small teams with clear missions

(14:29) A model for building products

(18:03) Jeremy’s thoughts on MVPs (minimum viable products)

(22:26) Designing for the most complex use case first

(23:17) What a compound startup is and how it works at Rippling

(27:09) Rippling’s unique culture of fast decision-making

(28:14) Rippling’s leadership values

(32:13) Advice for cultivating fast-decision-making teams

(33:44) How deep-level thinking and working on the ground helped Rippling expand to other countries

(38:42) Why product leaders need to be right

(40:42) How Rippling decided where to expand to first

(42:29) The case for expanding internationally before you think you’re ready

(45:32) Why Jeremy isn’t a huge fan of frameworks

(48:08) The differences between building product at Rippling and Coinbase

(52:49) How Jeremy hires PMs at Rippling

(58:29) Advice for junior PMs

(1:00:19) Lessons from working with a founder who has strong opinions about what the product should be

(1:02:15) Lightning round

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Referenced:

• Coinbase: https://www.coinbase.com/

• Ethereum: https://ethereum.org/en/

• Parker Conrad on Twitter: https://twitter.com/parkerconrad

• Rippling: https://www.rippling.com/

• Excellent Advice for Living: Wisdom I Wish I’d Known Earlier: https://www.amazon.com/Excellent-Advice-Living-Wisdom-Earlier/dp/0593654528

• Matt MacInnis on Twitter: https://twitter.com/stanine

• Rippling’s leadership principles: https://www.rippling.com/life

• Airbnb cereal story: https://www.cnbc.com/2023/04/18/airbnb-ceo-says-he-wooed-first-investors-with-boxes-of-cereal.html

• Guidewire: https://www.guidewire.com/

• Jira: https://www.atlassian.com/software/jira

• Kyle Boston on Twitter: https://twitter.com/KyleB

• Quicksilver (book one of the Baroque Cycle series:) https://www.amazon.com/Quicksilver-Baroque-Cycle-Vol-1/dp/0060593083/r

• Consider Phlebas (book 1 of The Culture series): https://www.amazon.com/Consider-Phlebas-Culture-Iain-Banks/dp/031600538X/

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• The Game on Paramount+: https://www.paramountplus.com/shows/the-game-2021/

• Tenet: https://www.imdb.com/title/tt6723592/

• Corsair H60 CPU cooler: https://www.amazon.com/CORSAIR-Hydro-Liquid-Cooler-Radiator/dp/B00A0HZMGA

• Focal Bathys headphones: https://www.amazon.com/Focal-Over-Ear-Bluetooth-Headphones-Cancelation/dp/B0B93YKQT3

• Pandemic: https://www.amazon.com/Z-Man-Games-ZM7101-Pandemic/dp/B00A2HD40E

• Gloomhaven: https://www.amazon.com/Cephalofair-Games-CPH0201-Gloomhaven/dp/B01LZXVN4P

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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