LLenny's Podcast
← All episodes
Jeremy Henrickson (Rippling, Coinbase)04 June 2023

Moving fast and navigating uncertainty

8Frameworks
15Insights

Frameworks in this episode

Innovation7 steps

Design for the Most Complex Use Case First

Architect for the hardest customer you'll ever have, then choose what to ship first.

Read →
Leadership6 steps

Go and See: Walking All the Way to Ground

Product leaders become the world's foremost expert in their domain by going to the source themselves.

Read →
Strategy5 steps

Imperatives: The Cross-Team Must-Do List

A short force-ranked list every team must absorb — defined by what it excludes.

Read →
Strategy7 steps

International Market Entry Stack Rank

Assume you'll need everywhere, order by demand, then re-rank by build cost, strategic value, and long poles.

Read →
Leadership6 steps

The Assumption-Break PM Interview

Give a case study too big to solve, break one assumption, and watch whether they rattle off the implications.

Read →
Leadership7 steps

The Decision Tempo System

Never leave a decision in the room: decide now, pull in whoever is missing, and let deadlines actually bite.

Read →
Productivity5 steps

The Four Levers of Velocity at Scale

Small missions, a real platform, leaders in the trenches, and a team you keep recalibrating.

Read →
Entrepreneurship8 steps

The Internal Founder Pod

One entrepreneurial engineer, one designer, a platform apprenticeship, and a new product line in 6-9 months.

Read →

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster44:00

You Can't Just Drop Your US Product Into Another Country

The most surprising lesson Jeremy keeps relearning is that every country is genuinely unique and you can't just port your US approach abroad. Other countries find it insulting, and everyone believes their local context is special. It comes down to details like whether 'color' has a u in it, or a demo showing a US social security number, that instantly destroy credibility no matter how good the rest of the product is.

  • Every country is unique; you can't drop a US approach into another market
  • Other countries find a straight port insulting and believe their context is special
  • Small details like the spelling of 'colour' signal whether you respect the local context
  • A demo exposing a US social security number instantly loses credibility abroad

“every country is unique you can't just like you can't just take your us-based approach and like Drop it into another country other countries find…”

Jeremy Henrickson · 44:30

“people in the UK really really care if there's a u in color right just as we care if there's not a u in color…”

Jeremy Henrickson · 43:00
#international-expansion#localization#product-strategy

Hot Take· 4

Hot Take05:30

How to Keep a Team Focused While Everyone Around You Gets Rich

Asked how he kept his Coinbase team focused during the crypto mania, Jeremy says the first rule is you simply don't talk about people getting rich. You reframe everything around customers and their money, and you make security the non-negotiable number-one priority. A security leader's ability to frame fast decisions in terms of what's still safe let the team move quickly without cutting corners.

  • Never frame the work around people getting rich; frame it around customers and their money
  • Security was always the number-one priority, no matter how fast they moved
  • A trusted security leader put rapid decisions in context of what could still be done safely
  • Focus meant balancing immediate fires against where the product needed to be in six months

“well the first thing is you don't talk about people getting rich it's like it's a it's a very technical it's a very technical you…”

Jeremy Henrickson · 05:30
#focus#security#crypto#culture
Hot Take18:00

Why Rippling Deliberately Avoids the MVP

Jeremy isn't anti-MVP in general, but argues an MVP would do a disservice to both Rippling's customers and the team building it. Optimizing for speed minimizes the deeper product thinking about what fully differentiates the product, and worse, it leads engineers to make simplifying architectural assumptions that are extremely hard to unwind after months of building on top of them.

  • MVPs have their place, especially at a true zero-to-one company with no market validation
  • Optimizing for speed minimizes deeper thinking about differentiation and future needs
  • Worse, it leads to building the wrong thing technically
  • Simplifying assumptions get buried under hundreds of later decisions and are hard to unwind

“a minimum viable product would do a disservice like to both our customers and to like the very team that was building it”

Jeremy Henrickson · 18:00

“worse it leads to building the wrong thing technically right”

Jeremy Henrickson · 19:00
#mvp#product-strategy#architecture#rippling
Hot Take27:00

Rippling's Culture of Making Decisions Today, Not Next Week

Jeremy says Rippling's most distinctive trait is sheer speed of execution and decision-making. Rather than scheduling a meeting for next week, they make the call in the current meeting or Slack-call whoever is needed to close it out that day. Deadlines are real, and it genuinely shocks newcomers when the company moves on past a missed date rather than letting someone slow everyone down.

  • The defining cultural trait is speed of execution and decision-making
  • Decisions get made inside the meeting, pulling in whoever is needed rather than deferring
  • Some irreversible decisions can't be made that way, but most benefit from tempo
  • Deadlines hold: the company moves on past a missed date, which surprises new hires

“let's not schedule a meeting for next week or tomorrow or later today you know we're in the middle of the meeting we need to…”

Jeremy Henrickson · 27:30

“no no that date passed you know what you don't get to like retroactively like like make everybody react to the fact that you didn't…”

Jeremy Henrickson · 30:00
#decision-making#velocity#culture#rippling
Hot Take45:30

Anti-Process, Not Anti-Framework

Jeremy clarifies he's not anti-framework but anti-process as a substitute for deep product thinking. He wants just enough process to create a frame for good decisions and no more, warning that scaling companies fool themselves into thinking better Jira categorization will produce good prioritization. He refuses to dogmatically mandate scrum or kanban; the right amount of process depends entirely on a team's specific stage.

  • Not anti-framework, but anti-process as a substitution for deep product thinking
  • Want just enough process to frame good decisions and no more
  • Perfect Jira categorization won't substitute for deciding what's actually important to build
  • Refuses to mandate scrum or kanban; the right process depends on each team's life cycle

“I am anti-process as a substitution for deep product thinking right so I like to have just enough process to create a frame”

Jeremy Henrickson · 46:00
#process#frameworks#product-management#prioritization

Explainer· 1

Explainer23:30

What a Compound Startup Is and Why the System of Record Matters

Jeremy explains Rippling as a compound startup: many businesses (payroll, benefits, IT, device management) that each rival multi-billion-dollar standalone companies, all built on one platform. Parker's founding insight was that without a single system of record, data gets replicated and falls out of sync everywhere. Starting from a single source of truth lets Rippling do things like instantly know an employee's manager, which are literally impossible for competitors stitching integrations together.

  • A compound startup is many businesses that all work together on one shared platform
  • Each product line (payroll, benefits, IT) rivals standalone multi-billion-dollar companies
  • Without a single system of record, data is copied and impossible to keep in sync
  • One source of truth enables capabilities competitors can't replicate, like always-correct org structure

“the right answers to have a single system of record one place one database where all of that information is resident”

Jeremy Henrickson · 24:00

“our ability to kind of differentiate right boils down to kind of that one fundamental decision which just allows us to do things that are…”

Jeremy Henrickson · 26:30
#compound-startup#platform#system-of-record#differentiation

Story· 3

Story04:00

Leading Product at Coinbase Through 2017's 40x Growth

Jeremy recounts leading product at Coinbase in 2017 as crypto exploded into public consciousness and usage grew 40x in a single year. He describes it as both a dream and a nightmare, with systems breaking on the edges every Saturday morning when people traded. The experience taught him hard lessons about who you choose to work with and staying focused under pressure.

  • Coinbase saw over 40x growth in usage across 2017 as crypto took off
  • It was simultaneously a dream come true and a nightmare to operate
  • Systems repeatedly broke on the edges, often on Saturday mornings when trading spiked
  • The biggest lessons were about who you trust and keeping the right people in the room

“experienced over the course of 2017 40x growth in in usage that's like a dream come true for for a lot of people”

Jeremy Henrickson · 04:30

“people like to trade crypto on Saturday mornings and so a lot of Saturday mornings there's like some new like like thing would break on…”

Jeremy Henrickson · 05:00
#coinbase#crypto#scaling#leadership
Story12:00

How a Four-Person Team Built Rippling's Time & Attendance Product

Jeremy shares how Rippling built its time and attendance product with a single talented systems engineer capable of product thinking, plus a few people he recruited, all with CEO Parker spending time on it. Those roughly four people shipped the product over nine months while being monomaniacally focused on only that one thing. He argues the speed came mostly from the small, focused team, not just from having the CEO unblocking things.

  • Started with one entrepreneurial systems engineer who could also do product thinking
  • A team of about four shipped time and attendance in around nine months
  • They worried only about their product, integrating minimally with the rest of the suite
  • The velocity came mostly from being small and focused, not just CEO involvement

“it was the only thing they were doing they didn't have to worry about what was going on with our payroll product”

Jeremy Henrickson · 13:00

“they were they were mono maniacally focused on this one thing”

Jeremy Henrickson · 13:00
#rippling#small-teams#velocity#product-development
Story20:30

Launching Global Payroll With Six Countries Instead of Copying the US

Jeremy uses Rippling's global payroll product as an example of designing for the complex case first. The fast path would have been to copy the US system and tweak it for one country like the UK. Instead they launched with six deliberately different countries, forcing a system where roughly 80% is shared platform and the country-specific 20% can often be configured by compliance or legal staff rather than expensive engineers.

  • The fast option was to replicate the US system and change surface details for the UK
  • They instead launched six deliberately different countries with different HRIS and EOR needs
  • Result: about 80% of the system is shared global platform, 20% is country-specific
  • Most country specifics can be configured by compliance or legal, not costly engineering changes

“we need to launch with six countries and these are six Super different countries that we that we want to like look at”

Jeremy Henrickson · 21:00
#global-payroll#rippling#product-strategy#international

Q&A· 1

Q&A53:00

What Jeremy Looks for When Hiring Product Managers

Jeremy interviews PMs with a case study deliberately too complex to fully answer, then changes one assumption to watch how they react. Strong candidates immediately spot the cascade of implications and rattle them off; weaker ones get flummoxed. He also weighs the insightfulness of the questions candidates ask him, which signals both genuine interest and the depth of their thinking.

  • The case study is intentionally too large for anyone to have all the answers up front
  • Changing one assumption reveals how deeply and quickly a candidate thinks
  • Strong candidates instantly enumerate the downstream implications
  • The quality of the questions candidates ask signals real interest and depth

“oh well that has like these 400 implications right and they just start rattling them off”

Jeremy Henrickson · 54:00

“the insightfulness of the questions that people ask which is indicative of number one they're like actual interest in the job”

Jeremy Henrickson · 54:00
#hiring#product-management#interviewing

Takeaway· 5

Takeaway06:30

Debate Hard, Then Go Full Speed Until You Change Direction

In crypto, fundamental questions like whether Ethereum would even survive had no clear answer, only strong opinions. Jeremy's approach was to have the debates fully, then come out with a single clear company point of view and commit to it completely. You go full speed toward that answer until you deliberately decide to go full speed toward a different one.

  • Crypto's deep uncertainty meant simple questions had no agreed answers, only strong opinions
  • You have to allow real debate because so much is genuinely unknown
  • After debate, converge on one clear company point of view everyone shoots toward
  • Commit fully to that direction until you consciously choose a new one

“you go full speed toward this answer until you decide to go full speed toward a different answer”

Jeremy Henrickson · 07:00
#decision-making#uncertainty#alignment
Takeaway32:30

Go and See: Product Leaders Must Walk All the Way to Ground

One of Rippling's leadership principles is 'go and see' — walk all the way down to the engineer writing the code, because top-level communication is always insufficient to reveal what really matters. Jeremy applies this to becoming a genuine domain expert: the team lead for global payroll personally studied the tax laws of each country before hiring specialists. He estimates it can consume half your working hours, but you can't understand a product without it.

  • 'Go and see' means walking down to the engineer writing the code, not delegating understanding
  • Top-level communication is always too coarse to reveal what truly matters
  • A product leader personally studied each country's tax laws before hiring a tax specialist
  • Becoming the world expert can take roughly half your hours but is non-negotiable

“go and see right so to to to look at the thing and then like walk all the way to ground and like talk with…”

Jeremy Henrickson · 33:00

“if a job is 80 hours a week it's like 40 of your hours”

Jeremy Henrickson · 37:30
#leadership#domain-expertise#product-management#rippling
Takeaway42:30

Expand Internationally Earlier Than You Think You Need To

On when to start expanding internationally, Jeremy's answer is always earlier than you think, because it's harder and more specialized than anyone expects who hasn't done it. Rippling holds a firm thesis that companies not going global in payroll, benefits, and IT won't be around in ten years, a trend Covid dramatically accelerated by pushing even very small companies to become multi-country.

  • The right time to go international is always before you think you need to
  • It's harder and more specialized than first-timers expect
  • Rippling's thesis: non-global companies in payroll/benefits/IT won't survive ten years
  • Covid pushed multi-country operations down to even very small companies

“I think the right answer to that question is always before you think you do before you think you need to”

Jeremy Henrickson · 42:30
#international-expansion#strategy#timing
Takeaway58:30

The Best Early-Career PM Advice: Be Humble

For early-career PMs, Jeremy's advice is to be humble. Product work by definition means living in a world where no one knows the right answer yet, because if someone did they'd have already built it. Only by acknowledging what you don't know can you stay open to absorbing information and reaching new conclusions; PMs who cling to how smart they were in school close themselves off.

  • Be humble; product work means no one knows the right answer yet
  • If someone already had the answer, they'd have built it
  • Humility keeps you open to absorbing and synthesizing what you don't know
  • The job is always about discovery, curiosity, and elasticity of thought

“being a product person means that like by definition you're living in a world where like no one knows the right answer yet because if…”

Jeremy Henrickson · 58:30
#career-advice#product-management#humility
Takeaway1:05:00

'Imperatives': The Force-Ranked List Whose Power Is What's Left Off

Jeremy's most recent innovation at Rippling is what he calls imperatives: a force-ranked list of things everyone across product and engineering must do. The power of the list is in what it excludes; drawing hard lines about the roughly ten cross-team priorities created far more focus and clarity than before, and each team folds those into their own priorities.

  • Imperatives are a force-ranked list of things everyone across product and engineering must do
  • The important part is the things deliberately left off the list
  • They typically run around ten cross-team imperatives at once
  • Each team factors the imperatives into their own priorities

“the kind of introduction of what I'm calling imperatives these things that whether they come bottom up or top down are things that like everybody…”

Jeremy Henrickson · 1:05:00

“what's important about that list is the things that are not on it”

Jeremy Henrickson · 1:05:30
#prioritization#focus#rippling#execution