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

Product leaders should go deep on a problem to gain insights, rather than just delegating tasks to their teams. Being present with the people in the trenches helps them understand the challenges and successes. This approach helps achieve scale and maintain focus, and build a culture of fast decision-making. It is also crucial to have the right people in the right place at the right time, especially during challenging times like the crypto market boom in 2017. Leaders should prioritize security aspects and focus on the customer's needs instead of the team's personal gains. By doing so, product leaders can become world experts in their domains.

Maintaining velocity at scale requires small teams with clear missions and breaking down large problems into sufficiently small bits that small teams can attack wholeheartedly. Developing a clear platform with a clear interface that is easy for both engineers and product people to use also simplifies the space in which people have to think about these problems. During times of intense work, it's important to take a step back and talk with friends or others about what's really going on in order to set it in the context of the future and what can be learned from the experience. In the midst of uncertainty, it's important to have debates, but then come out of those conversations with a clear company point of view that everyone is shooting towards.

Platforms need an iterative approach with the right people who can do both systems thinking and product thinking simultaneously. Leaders should dive deep into the trenches to understand challenges and problems. Teams should have the right distribution of experience and seniority, and people should be doing what they love. Clear and precise product leadership, along with building small, focused teams, can accelerate growth over time. Rippling's model of starting new things with small groups and focusing on a single task allows for quicker execution and success.

Rippling's approach to adding a new business unit or product feature involves finding a single engineer who is entrepreneurial and can operate at a high tempo, along with a design partner who is skilled in UX and interaction design. They work together to build the product quickly and launch it within six to nine months, often starting with a one-page view of what needs to be built. The focus is on finding a balance between speed and comprehensiveness, while constantly pressure testing designs and getting feedback. The approach allows for anyone in the organization, regardless of their position, to look at what's happening and make decisions without interference from the management structure.

Designing for the most complex use case first is crucial for building a product that can accommodate future growth and prevent the need for unwinding decisions made in the past. While MVPs have their place, they may lead to building the wrong thing technically and limiting product creativity. At Rippling, they followed this approach when building their global payroll product, which not only accommodates complex use cases but also makes adding new countries easier. While it may take a bit more time initially, designing for the most complex use case saves time in the long run and prevents building a product that does a disservice to customers and the team.

Rippling is a compound startup which means it is made up of multiple businesses that work together on a single platform. This approach allows them to have a single system of record for all their data which makes it easier for their downstream systems to have the right data at the right time. Having a single system of record makes it possible to build things like workflow, reporting, analytics and permissioning systems. Rippling is able to do this because they have spent a considerable amount of time building the different versions of their products and integrating them into one platform. Building a single system of record is better for many reasons like having a single source of truth and makes complex tasks like building a permissioning system possible.

Rippling's system of record enables them to do things that are literally impossible for any other company to do. They solve the most complex use case first which allows all the data to be in the same place. Rippling's culture revolves around speed of execution and decision-making. They value the tempo of decision-making and the speed of response which is partly due to the fact that they are a compound startup with small independently operating teams. The ability to make decisions quickly is something that everybody promulgates. They have a timeline for decision-making which doesn't leave much room for delay. If you are an expert in your domain, then you can give solutions off the top of your head. Rippling's culture gets reinforced on its own, out of its gravity.

Creating and communicating clear priorities and expectations is essential for moving faster and making better decisions in a company. Going to the ground and talking to team members is necessary to understand the nuances and achieve that level of clarity. The leadership principles should reflect the culture and reflect what makes people successful in the organization, and HR teams can use platforms like Lenny's Jobs to access a curated list of professionals who are looking for new opportunities. Going beyond the top-level communication and engaging with team members creating clear expectations creates a culture of clarity and forces everyone to up their game, leading to better performance and fulfillment.

To build a successful product, it's important to understand and learn firsthand about the details of every aspect of the product, be it technical, design, regulatory, or governmental. One cannot delegate this responsibility to someone else, as a product leader must become a world expert in every aspect of the product before being able to hire specialists. It may take up to half of the job time to become a master in tax laws of different countries, as it's essential to understand how they work, how they communicate, and handle them. Great product leaders have native curiosity, interest, and the ability to absorb a lot of stuff, making them capable of knowing the full scope of the product.

Product leaders need to be 'right' most of the time because their decisions impact the entire organization and spending time and energy. Leaders who can make complex decisions with incomplete information and confidence are highly valuable. Companies must expand globally to pay employees and have their information in their HR system anywhere in the world. To decide which countries to expand to, the company listed out the countries where their US-based companies had employees and ranked them based on how hard it is to build in these countries and its strategic value. The early decisions were reordered over time as the company learned more about the countries, but the basic list is mostly right.

Expanding internationally is crucial for the survival of companies in the long run, particularly in industries like payroll, insurance, benefits, and IT. It's essential to start the process earlier than you think you should, as it takes a long time to absorb the cultural lessons necessary to succeed in other countries. The most significant challenge is adapting to every country's unique context and respecting and integrating their cultural nuances. Frameworks and processes are beneficial but should only be used to create a frame for decisions, not as a substitute for deep product thinking. Process-based decision-making can hinder progress and delay growth, while data analysis and research can help prioritize effectively.

Process and frameworks in product development should be context-specific and dependent on the team's lifecycle. Dogmatically sticking to one framework is counterproductive and can be harmful. Quarterly planning and Jira are essential for unification and rationalizing about progress. The crypto and product development domains have different decision-making processes due to the predictability and ambiguity of the market and the level of cognitive dissonance. The day-to-day velocity of decision-making is higher in Rippling due to the absence of ambiguity and uncertainty. Reactivity to the environment and uncertainty of the regulatory environment are significant factors in the crypto domain.

Even though jobs can be stressful at times, the memories and relationships built during those times can be valued for a long time. The learnings from experiences that did not work out traditionally end up being incredibly valuable, in all these unexpected ways. Product managers who are mentally agile and able to react to changes in problem-solving are effective. Inquisitiveness is a good sign of personal interest in a job and shows a willingness to learn. A person's ability to answer questions is indicative of their ability to understand a problem and is very essential while hiring for PM positions.

Asking insightful and thought-provoking questions during an interview is important as it showcases the candidate's ability to think critically and deeply about the business. While the quality of questions can vary, a candidate who raises questions that show an understanding of the company's context and reveals a depth of thinking is highly desirable. Additionally, the ability to ask detailed questions is a crucial trait for product managers as it helps them navigate complex businesses. Employers should create prompts that are specific to their business, and they should always ask the candidate what questions they have for them. This curiosity and interest in the role are strong signals of a candidate's engagement and suitability for the position.

Being humble is the key to success in the early part of a product manager's career. Acknowledging the things you don't know, maintaining curiosity and elasticity of thought helps uncover new insights and ideas. Great leaders are always willing to change their minds when faced with new information or when they realize they were wrong. Moreover, being adaptable to the personalities and opinions of your co-workers is essential, especially when working with a product-minded founder. Having a deep foundation of respect and being moldable helps build a positive working relationship. Finally, adaptability is an important attribute in the product world, which allows one to fit in and work effectively with different personalities and work environments.

Recommendations of books and products can be a great source of inspiration. The Baroque Cycle by Neal Stephenson and the Culture series by Iain Banks are highly recommended books by Jeremy Henrickson. Focal Bathys headphones and Corsair H60 CPU cooler are two products which he recently discovered, and he highly recommends them. An introduction of imperatives by Rippling has created more focus and clarity on priorities for everyone in the product and engineering team, resulting in better execution. These minor changes in the approach can have a larger impact on the overall productivity of the team.

Cross-team collaboration is a natural part of a company's evolution, especially during globalization and large platform improvements. Companies need to work on multiple tasks simultaneously, and it's essential to have a solid team for this. Pandemic Legacy and Gloomhaven are two exciting family board games to play together, where everyone can learn about strategy. Surfline.com is hiring senior entrepreneurial PMs, and interested job seekers can visit the website's career section to explore those roles. LinkedIn is the easiest way to get in touch with the speaker, and he's looking for candidates who align with their leadership principles. Cross-team collaboration should be a priority, and employees who enjoy board games can create unique learning opportunities for their families.