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Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)

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 — Brought to you by Miro—A collaborative visual platform where your best work comes to life | Mixpanel—Product analytics that everyone can trust, use, and afford | Lenny’s Job Board—Hire the best product people. Find the best product gigs Find the transcript at: https://www.lennysnewsletter.com/p/moving-fast-and-navigating-uncertainty Where to find Jeremy Henrickson: • Twitter: https://twitter.com/jeremyhenricks • LinkedIn: https://www.linkedin.com/in/jeremyhenrickson/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Jeremy HenricksonguestLenny Rachitskyhost
Jun 3, 20231h 8mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jeremy Henrickson on building fast, deep, globally scalable product organizations

  1. Jeremy Henrickson, SVP of Product at Rippling and former CPO at Coinbase, shares how he maintains product velocity in hyper-growth and high-uncertainty environments.
  2. He emphasizes small, founder-like product teams, deep domain immersion by product leaders, and a culture of extremely fast, high-quality decision-making.
  3. Henrickson argues against shallow MVPs in favor of designing for the most complex use cases first, especially when building on a shared platform or system of record.
  4. He also covers global expansion strategy, Rippling’s “compound startup” model, hiring and evaluating PMs, and how to effectively partner with a strongly opinionated, product-centric founder.

IDEAS WORTH REMEMBERING

5 ideas

Use small, entrepreneurial teams with clear missions to preserve speed at scale.

Rippling repeatedly seeds new products with a ‘founder-type’ engineer plus a designer and a tiny team focused monomaniacally on one problem, enabling rapid learning, direct access to leadership, and minimized coordination overhead.

Design for the most complex use case first instead of a thin MVP.

Henrickson argues that optimizing for speed via simple MVPs often bakes in the wrong technical and product assumptions; instead, you should model for the hardest future scenarios (e.g., 10,000 global employees, multi-country payroll) even if you only ship simpler flows initially.

Invest in a real platform and single system of record to unlock compounding advantages.

Rippling’s core differentiation comes from one shared employee data store underlying many ‘vertical’ products, enabling capabilities like unified permissions, accurate reporting, and cross-product workflows that point solutions literally cannot match.

Cultivate a culture of very fast, high-quality decision-making.

Decisions are made “now,” not next week: leaders pull the right people into live conversations, operate on aggressive planning timelines, and actually move on if a team misses a decision deadline, which keeps organizational tempo high.

Product leaders must ‘go and see’ and become genuine domain experts.

Rather than delegating details to specialists, PMs are expected to deeply study tax codes, country regulations, or technical constraints themselves; that depth is what enables sound product judgment and scalable architectures.

WORDS WORTH SAVING

5 quotes

You have to go full speed toward one answer until you decide to go full speed toward a different answer.

Jeremy Henrickson

A minimum viable product would do a disservice to both our customers and to the team building it.

Jeremy Henrickson

We design for the most complex use case first, even if we don’t support it in version one.

Jeremy Henrickson

No company I’ve been at, at any scale, has ever operated at the tempo this one does.

Jeremy Henrickson (on Rippling)

What’s the point of writing a document if you don’t know what you’re talking about?

Jeremy Henrickson

Scaling product and teams during hyper-growth and market uncertainty (Coinbase experience)Maintaining velocity at scale through small teams, platforms, and decision tempoRippling’s compound startup model and single system of record as core differentiationDesigning for complex use cases first vs. traditional MVP thinkingGlobal expansion strategy: choosing markets, local nuance, and payroll complexityLeadership principles: go and see, speed of execution, leaders being right a lot, changing mindsHiring and developing product managers, including interviews, case studies, and early-career advice

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