Jeremy Henrickson
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.
AI & Technology Skills
A well-defined platform with clear interfaces simplifies product development by reducing the cognitive load on individual teams.
"The more you can bake into a clear platform, it reduces the decision-making complexity for everyone who's working on the domain part of the problem."
A 'compound startup' leverages a single system of record to allow multiple vertical products to share data and underlying capabilities seamlessly.
"The idea of a compound startup for us is that we're basically a lot of businesses that all work together... all of these different businesses benefit from being built on top of one platform."
Hiring & Teams Skills
The quality and insightfulness of a candidate's questions are often the strongest signal of their potential and engagement.
"My favorite one is 'What questions do you have for me?' by far... it is again indicative of these things that people have thought through or not thought through or the depth that they're thinking or t..."
Use complex, ambiguous case studies to test a candidate's mental agility and ability to handle shifting information.
"An important part of the case study is that it's actually too complex for people to have all of the answers upfront... seeing how people react to that is really indicative of how deeply they understan..."
Leadership Skills
Effective leadership requires 'diving deep' into the most complex problems rather than just delegating from a high level.
"It's very, very tempting to float up here as a leader and say, 'Hey, you take that hill over there. You guys do this over here.' When in fact, where you really learn where the challenges are, or the p..."
Success with strong-willed founders requires high adaptability and a foundation of mutual respect.
"You have to find a way to work with those [manager's idiosyncrasies]. And I think that adaptability, like I'm just sort of, I like being a moldable puzzle piece where I can just fit in."
High-velocity organizations prioritize immediate decision-making over scheduling future meetings.
"We're in the middle of a meeting, we need to make a decision. Let's either make the decision or if we can't, let's Slack call in the person that we need in order to make that decision. And we'll be do..."
Process should facilitate thinking rather than replace it; the right amount of process depends on the team's specific lifecycle.
"I am anti-process as a substitution for deep product thinking... I like to have just enough process to create a frame so that the right decisions can happen and no more."
Product Management Skills
True understanding of a problem requires 'going to ground' and engaging with the lowest level of execution.
"Go and see. Right? So to look at the thing and then walk all the way to ground and talk with the engineer who's writing the code on the thing. Because inevitably this top-level communication is insuff..."
Product managers must become domain experts by studying primary sources (like tax laws) rather than delegating all research to specialists.
"The person with the product thing has to get into those same weeds first to really understand it... what's the point of writing a document if you don't know what you're talking about?"