Moving Fast & Navigating
Uncertainty at Scale

Jeremy Henrickson

CPO, Rippling · Former CPO, Coinbase

JUN 4 2023

Core Model

The Compound
Startup

Parker Conrad's original insight: every HR vertical already has billion-dollar incumbents, but they all replicate the same data. One system of record, with every product stacked on top, unlocks things none of them can do alone.

"Having a single system of record is better for many reasons, but more importantly, without it there's a whole class of things you simply can't build."

Framework

4 Laws of Velocity at Scale

40×

Coinbase growth 2017

people to start a product line

9mo

blank sheet to shipped product

Small teams, clear missions: Dunbar's number is real. Break the big problem into bits small groups can attack wholeheartedly, minimise horizontal communication at all costs.
Invest in platform: A clean platform interface shrinks the decision space for every product built on top. It compounds, more investment means engineers do more with less over time.
Dive deep as a leader: Don't float up and point at hills. Get in the trenches on the hardest, most complicated thing. That is where you find the actual challenges, problems, and successes.
Match skills to lifecycle: Zero-to-one heroes can be wrong for scaling. Constantly ask, does this person love what they're doing now? Recalibrate before frustration sets in.

Rippling's new-product playbook One entrepreneurial engineer + one design partner → onboard to the platform for a few months → recruit 2–3 more → ship in 6–9 months → scale the team only if the product demands it.

Deep Dive

Design for Complexity First, Then Move Fast

Jeremy's anti-MVP thesis: building only the simple case bakes in architectural assumptions that take years to unwind. Instead, understand the most complex use case first, even if you don't ship it, so the foundations survive it later.

Rippling Global Payroll: could have cloned the US product for one country. Instead launched in 6 very different countries simultaneously. Now adding a country is 80% platform, 20% custom, and the custom parts are handled by compliance staff, not engineers.
"Go and See": Rippling's leadership principle. The payroll head personally opened each country's tax law before engineering started, not delegated to a specialist. You must get into the weeds before you can write a worthwhile document about them.
World-expert rule: Every PM owns their product entirely and is expected to be the world's foremost expert on it. That depth makes fast decisions possible without scheduling a meeting.
Imperatives: A force-ranked list (~10 items) of cross-team priorities every product and engineering team must factor into their own planning. Removes ambiguity on what actually matters globally this quarter.

Decision tempo at Rippling

Quarterly planning has hard deadlines. If you miss the window, the company moves on, no retroactive replanning. Every irreversible decision gets proper deliberation; everything else gets decided today, in this meeting, with a Slack call to whoever is needed.

Leaders are right a lot

Product leaders spend time, energy, and company credibility with every call. The ability to enter ambiguous situations with incomplete information and come out with the right answer is the rarest, and most valuable, PM skill. It cannot be taught; you evaluate it in retrospect.

Coinbase vs Rippling

At Coinbase: the challenge was navigating deep uncertainty, is Ethereum even a thing? At Rippling: the challenge is differentiation via platform depth. Same mental model, very different environments and resulting velocities.

Tactics

Hiring PMs & Working with Strong Founders

Case-study stress test: Make the problem too big to solve upfront, then change one assumption mid-interview. Watch how fast they trace the 400 downstream implications.
Best interview question: "What questions do you have for me?", asked before the product discussion. Depth, curiosity, and genuine excitement all surface here first. An unexpectedly insightful question is the strongest signal.
Early-career advice: be humble. No one knows the right answer yet, that is the entire job. Closing yourself off kills the curiosity and elasticity a PM needs most.
Great leaders change their minds a lot. Being in a culture where saying "I was wrong" is safe is as important as the individual trait itself.
Working with opinionated founders: First, verify they're willing to be challenged. Then become a moldable puzzle piece, build respect before debates, and find where to push vs. where to align.

International expansion rule Start before you think you need to. It is harder and more specialised than any first-timer expects, and every country finds it insulting if you just drop your US product on them unchanged.

Contrarian

Myths About Building at Velocity

✗ MVPs are always the right starting point INSTEAD → ✓ MVPs optimise for speed but bake in wrong architecture. Understand the most complex case first, even if you don't ship it, or you will spend years unwinding assumptions you never knew you were making.

✗ Process and frameworks create velocity INSTEAD → ✓ Deep product thinking creates velocity. Use just enough process to frame decisions, no more. Dogmatically adopting a framework is a substitute for thinking, not an enabler of it.

✗ Senior leaders should point at hills, not climb them INSTEAD → ✓ The biggest mistakes hide at ground level. Get in the trenches on the hardest thing, not to micromanage, but because that is the only place you discover what actually needs fixing.

✗ International expansion can wait until you are ready INSTEAD → ✓ Start earlier than you think you need to. COVID proved even tiny companies go global overnight. Cultural adaptation takes far longer than any technical build, the window is always earlier than it looks.

The CompoundStartup

4 Laws of Velocity at Scale

Design for Complexity First, Then Move Fast

Hiring PMs & Working with Strong Founders

Myths About Building at Velocity

The Compound
Startup