Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)
Jeremy Henriksen, SVP of Product at Rippling (ex-Coinbase CPO), shares lessons on maintaining velocity at scale, fostering fast decision-making, product leaders deeply understanding their domain, and designing for complex use cases instead of MVPs.
Deep Dive Analysis
14 Topic Outline
Leading Product Teams at Coinbase During Crypto Boom
Maintaining Velocity and Focus at Scale
Rippling's Model for Starting New Products
The Case Against Minimum Viable Products (MVPs)
Understanding the 'Compound Startup' Model at Rippling
Cultivating a Culture of Fast Decision-Making
Importance of Product Leaders Going Deep ('Go and See')
Why Product Leaders Need to Be Right Often
Strategies for International Expansion
The Problem with Dogmatic Frameworks
Differences in Product Building at Rippling vs. Coinbase
Hiring Product Managers at Rippling
Advice for Junior Product Managers
Working with a Product-Minded Founder
5 Key Concepts
Compound Startup
A business model where many different business units or products are built on a single underlying platform and system of record. This approach ensures all data is consistent and allows for unique capabilities that are impossible with fragmented systems.
Designing for Most Complex Use Case First
An approach to product development that involves understanding the most challenging, high-scale scenarios from the outset, even if not immediately supported. This prevents technical debt and ensures the product's architecture can accommodate future complex requirements without costly re-writes.
Go and See
A leadership principle emphasizing that leaders must dive deep into the details of a problem or product, talking directly with those on the ground. This firsthand understanding is crucial for truly grasping challenges, problems, and successes, and for making informed decisions.
Leaders are Right a Lot
A leadership principle highlighting the necessity for product leaders to frequently make correct decisions, especially in ambiguous situations with incomplete information. Their decisions impact the entire organization and determine the effective use of time and resources.
Imperatives
A recent innovation at Rippling referring to a prioritized list of cross-team initiatives that every product and engineering team must factor into their work. This creates focus and clarity by explicitly stating what everyone needs to do, and implicitly what they don't.
6 Questions Answered
Maintaining velocity at scale involves having small teams with clear missions, investing in a robust platform to reduce decision-making complexity, leaders diving deep into problems, and ensuring teams have the right distribution of experience and seniority.
Rippling believes MVPs optimize for speed at the expense of deeper product thinking and can lead to technically flawed architectural assumptions. Instead, they design for the most complex use cases first to ensure future scalability and differentiation, even if those complex features aren't in the initial launch.
Rippling cultivates fast decision-making by encouraging immediate action rather than scheduling future meetings, setting clear timelines for quarterly planning with strict adherence, and expecting product leaders to be world experts in their domains to provide quick, informed answers.
Companies should expand internationally earlier than they think they need to, because the process is harder, more specialized, and requires more time to absorb cultural nuances than typically anticipated. Ignoring this can lead to being left behind as more companies become global.
Beyond standard qualifications, Rippling looks for candidates who demonstrate mental agility by reacting well to changing assumptions in case studies, and who ask insightful questions that reveal deep interest and understanding of the business, even pushing the interviewer to think deeper.
Junior PMs should cultivate humility, acknowledging that they don't have all the answers and are open to learning from others. Maintaining curiosity, elasticity of thought, and creativity in problem-solving is crucial for continuous discovery and growth in the role.
31 Actionable Insights
1. Design for Complex Use Cases
Instead of optimizing for MVPs, design for the most complex use cases first. Understand simple scenarios, but ensure technical and product design accommodates future global, complex scenarios, even if not supported initially, to prevent costly architectural rework.
2. Become World Expert First
As a product leader, personally go deep and become the world expert in your product’s domain before delegating to specialists. This foundational understanding is crucial for effective product thinking.
3. Dedicate Half Time to Deep Understanding
Dedicate significant time (e.g., 50% of your work week) to personally “going and seeing” and deeply understanding the product and its domain firsthand.
4. Implement “Imperatives” for Focus
Implement “imperatives” – a short, force-ranked list of 10-ish cross-team priorities that everyone in product and engineering must factor into their work. Crucially, clarify what is not on the list to enhance focus and clarity.
5. Immediate Decision-Making Culture
Foster a culture of immediate decision-making by avoiding delays. Make decisions on the spot, or immediately bring in necessary people (e.g., via Slack call) to resolve issues the same day.
6. Clarify Priorities (and Non-Priorities)
Top-level product decision-makers must be extremely clear about what the priorities are and, crucially, what they are not. This eliminates distractions and focuses the team on the core mission.
7. Small Teams, Clear Missions
To maintain velocity at scale, organize into small teams with clear missions. Break down large problems into sufficiently small bits for these groups to attack wholeheartedly, minimizing horizontal communication.
8. Invest in Clear Platform
Build and invest in a clear, easy-to-use platform with a well-defined interface. This reduces decision-making complexity for both engineers and product people working on domain-specific problems.
9. Expand Internationally Early
Start international expansion earlier than you think necessary. It is consistently harder, more specialized, and takes longer to absorb cultural lessons than anticipated.
10. Respect Unique Local Contexts
When expanding internationally, deeply respect and adapt to each country’s unique local context and cultural nuances. Avoid simply porting a domestic approach, as this can be perceived as insulting and undermine credibility.
11. Process Supports Deep Thinking
Avoid using process as a substitute for deep product thinking. Implement just enough process to create a framework for good decisions, but no more.
12. Cultivate Humility as PM
For early career PMs, cultivate humility and acknowledge that no one has all the answers in product development. Be open to absorbing new information, synthesizing it, and changing conclusions.
13. Maintain Curiosity, Elasticity
Maintain curiosity, elasticity of thought, and creativity throughout your product career. Avoid closing yourself off to new ideas or assuming you always have the right answer.
14. Leaders Model Fast Decisions
For a culture of fast decision-making, senior leadership (especially the founder/CEO) must deliberately model this behavior constantly across all interactions (Slack, meetings, in-person).
15. Strict Decision Deadlines
Implement and strictly adhere to firm timelines for decision-making in planning processes (e.g., quarterly planning). Move on if decisions aren’t made by the deadline to reinforce a culture of rapid execution.
16. Product Managers: World Experts
Expect product managers to become the world’s foremost experts in their product domain. This deep expertise enables them to make quick, informed decisions without extensive follow-up.
17. Clear Product Leadership
Product leadership must be extremely clear and precise about what needs to be done. This clarity, combined with platform investment, enables teams to accelerate their execution over time.
18. Recalibrate Team Skills
Continuously assess and recalibrate team composition, ensuring the right distribution of experience and seniority. Match individuals to tasks they love and excel at, especially as product needs evolve from zero-to-one to scaling.
19. Launch New Products with Entrepreneurial Engineer
For new product lines, find an entrepreneurial engineer (internal or external) capable of product thinking, pair them with a design partner, and have them recruit a small 2-4 person team to build and launch the product in 6-9 months.
20. Direct Senior Leadership Exposure
Ensure senior leadership is directly exposed to what’s happening at all levels of the organization, bypassing management layers when necessary. This fosters transparency and enables quicker feedback and decision-making.
21. Debate, Then Commit
In uncertain environments with strong opinions, encourage open debates to explore options. Once a decision is made, establish a clear company point of view and commit to it fully until a new direction is chosen.
22. Product Leaders Must Be Right
Product leaders must strive to be right most of the time, especially in ambiguous situations with incomplete information, as their decisions significantly impact the entire organization’s time and energy.
23. Leaders Change Minds, Admit Wrong
Great leaders are willing to change their minds based on new information and admit when they are wrong. Foster an environment where it’s safe for everyone to acknowledge mistakes and adapt.
24. Adapt to Strong-Opinion Founders
When working with a strong-opinionated founder, be adaptable and understand the dynamics of the relationship. Ensure the founder is open to being challenged and build a deep foundation of mutual respect.
25. Prioritize Global Markets Systematically
Prioritize international markets by first identifying immediate customer demand. Then, assess the difficulty and strategic value of building in each country, and finally consider risks and long lead times. Stack rank and revisit this list.
26. Prioritize Security, Customer Money
During periods of rapid growth and market frenzy, leaders should focus the team on security and protecting customer money, rather than discussing personal wealth. This grounds the team in core responsibilities.
27. Balance Immediate, Long-Term
Address immediate issues (e.g., site outages) while simultaneously setting a clear, long-term vision (e.g., 6-month goals) for product and backend to guide the team’s efforts.
28. Reflect on Stressful Periods
When experiencing intense, stressful work periods, take time to step back and talk with friends to gain perspective. Frame these experiences as opportunities for significant personal growth and learning for the future.
29. Use Complex Case Studies (Hiring)
In PM interviews, use complex case studies that are too large for upfront answers. This allows candidates to react to ad hoc questions or changing assumptions, revealing mental agility and deep problem understanding.
30. Value Insightful Candidate Questions
Pay close attention to the quality and insightfulness of questions candidates ask. Truly insightful questions, especially those that make you pause and think, are strong indicators of a good candidate’s interest and deep thinking.
31. Ask “What Questions Do You Have?” (Hiring)
Always ask candidates “What questions do you have for me?” early in the interview process. Their questions reveal the depth of their thinking, interest, and engagement in the role.
6 Key Quotes
It's very, very tempting to kind of float up here as a leader and say, hey, you know, you take that hill over there, you guys do this over here. When in fact, like where you really learn where the challenges are, the problems or the successes is by like just like being there with the people in the trenches on like one of the things, like whichever one seems hardest or most complicated.
Jeremy Henrickson
The strongest memories for me are during like 2017, where crypto, which had kind of been at its nadir in like early 2016, it kind of slowly started climbing out, just kind of took off and became a real thing in the public consciousness. And, you know, Coinbase, which at the time had, you know, an exchange just like on-ramp and off-ramp from fiat to crypto and back, experienced over the course of 2017, 40x growth in usage.
Jeremy Henrickson
I think the biggest challenge was that in crypto, there's just so much uncertainty in general, like simple questions like, is Ethereum going to be a thing, right? Are the subject of debate and no one actually at the time had an answer to that question.
Jeremy Henrickson
I think the right answer to that question is always before you think you do. Before you think you need to. Because, like, there are, it's harder than everyone. If they've never done it before, it's harder than you think it is.
Jeremy Henrickson
I am anti-process as a substitution for deep product thinking. Right? So I like to have just enough process to create a frame. Right? So that the right decisions can happen and, like, no more.
Jeremy Henrickson
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 somebody did, they would have already built it.
Jeremy Henrickson
1 Protocols
Rippling's Model for Starting New Products
Jeremy Henrickson- Identify a need for a new product and create a one-page overview.
- Find a single, entrepreneurial systems engineer capable of product thinking and operating at tempo, often recruited externally.
- Pair the engineer with a skilled design partner who understands Rippling's products and component library.
- The engineer spends a few months learning the Rippling platform, understanding what's easy/hard, and how other products were built.
- During this time, the engineer recruits a small team (2-4 other engineers) with a 'zero to one' mentality.
- The team begins building the product, monomaniacally focused on this one thing.
- Regularly meet with senior leadership (e.g., Jeremy or Parker) every couple of weeks for feedback and pressure testing designs.
- Aim to launch the product or have it ready for internal dogfooding within 6 to 9 months.
- After launch, grow and scale the team as needed, depending on product demands (e.g., from 4 to 15 people).