The Wisdom Wall

“I'm better off with single threaded leadership than not. And so you get single threaded leadership in a narrow and focused area for the customer. And you get that in a way that we have seen repeatedly is better than the alternative, which is a purely functional system with lots of these huge functional teams and each…”

“The reason I would argue that it makes sense for all the code market teams to remain centralized is because they can be completely square first and they can optimize for overall square growth, um, in a way that is effectively neutral.”

“companies use exceptional product market fit to paper over what is herky jerky, impatient, distracted behavior. Underneath the covers when you actually go talk to the leaders within those companies.”

“And so our principle is the first iteration that I want to see in an org design, it's only going to have boxes and arrows. I don't want to have any people names on it, like no people name, period. Show me multiple options, but never show me people names. And then we'll iterate to something that is less purist And…”

“So one of our Kind of little rules here is don't end up with a junk drawer team because that team is going to be miserable, right? And like the manager there is going to be like, why did you like give me this junk drawer team? And the PM is like, I don't want to work on this thing. Uh, cause it's a junk drawer. And so,…”

“any org design, it's going to have goals. It's going to have trade-offs and it's going to have compensating mechanisms. And you just have to pick what you're going to achieve and how you're going to solve for the trade-offs that come with it.”

“You get a shorter escalation path on decisions that are going to unblock product development and to a certain extent go to market as well. So if you are the GM for Square Point of Sale, for example, Everything that is more narrowly constrained to that space, the escalation path is very short because if you have a…”

“What do you lose? You lose some level of efficiency. And like, we know that there is some level of inefficiency baked into the system because sometimes you may not have the most efficient staffing model if you have multiple GMs. Uh, whereas if you had a more centralized system, you could do a little bit more load…”

“What you don't want to do is in essence, ship the org chart to your customers as it shows up on your website, or as it shows up in the hands of a salesperson, because that could create all the wrong incentives that leave the customers worse off.”

“In general, I want to see avoidance of central committees that like are in a position of kind of adjudication. We want to push decision-making to be as decentralized as possible. We want to be have decision-making spread throughout the organization as much as possible. We don't want the ivory tower committee that hands…”

“what we've seen through this crazy hiring spree over the last four years is that you've got kind of managers reporting to managers, reporting to managers and like four levels of the management chain. You're going to have two people reporting to each other and you look at it on our org chart and you're like, wait a…”

“And so the dimensions we evaluate on are product or platform, and if it's product oriented, then that looks like a GM role. If it's going to be a little bit more platform or product platform is what I would characterize it. That looks like an MDL role. And so we'll cut it that way. We'll create MDL roles when we…”

“it makes logical sense that you would have all of those products basically under the same GM's remit, because when they are under different remits, you may have cognitive dissonance in roadmaps. So Put them all under one GM. So payroll, team management, shifts, scheduling, HR services, all of them are targeted at…”

“this is a standalone product in the industry at large. And there are large incumbent behemoth companies out there that run this thing as a standalone product. And there's an entire company outside of Square. And so that should have its own GM. It should have its own P&L. It's already material today or it will be in the…”

“Then you have the product marketing teams that frequently also serve as the glue because product marketing teams sit in between GTM teams and the product development teams. And so they serve as a bridge between the GM and the GTM functions, but also between each other. So they can also serve as a bridge between GMs.”

“And I know a lot of people like that who will not leave their desks for that two month period because they need to get through annual planning because that is our mechanism for aligning hundreds of teams and thousands of people Across billions of dollars in gross profit on a one year time window. And so it's one of…”

“The general principle for us is that the higher up in the organization you are, and the broader your remit, the more square first we want you to be.”

“companies that are fundamentally one product in the end, but have for whatever reason, cut up that one product into multiple GMs and it eventually by and large does not work. You have to recognize whether you are in this ecosystem portfolio, multi-product circumstance, or if you are in the single product circumstance…”

“without kind of a long haul commitment, it just doesn't work, because it's not a system that a lot of people in tech may be super familiar with. And as a result of that, it takes time and effort and patience and hiring and leadership coaching in order to get it and to build a remit that actually makes sense”

“ensure that each of these teams can successfully last for at least 12 months. Because again, you want to design for durability. You want to know that the team doesn't have such a short runway of work that it is taking on something that is urgent, but short lived.”

“In terms of we're ready to go and we've announced it to the whole company, if you will, that time window is usually in the neighborhood of 48 hours or less. And so we want it done in a very concentrated burst because with so many people involved, despite everybody's best intentions, word starts to get around. And so…”

“And in a hyper empowered company with a huge degree of transparency, like square is, if something's going wrong, I will almost always hear about it. And if something is going right, I may or may not hear about it, but you know, if it's going wrong, I will hear about it and I have ways of finding. Uh, so, so if I don't…”

“the only way you scale is if over time you Push better decision making through the organization, but it doesn't happen magically. It doesn't happen by just saying, well, this used to be my decision. Now it's your decision. Like that's just one piece of the puzzle, but you're going to have to do other work around it. So…”

“If you didn't equip that manager with all the right whys and the right talking points and all the FAQs, now all of a sudden you've left that manager in an awkward spot where now they are basically guessing, filling in the blanks. And now all of a sudden you have this kind of chain of lost in translation across people.”

“org design is effectively one among several tools in your management toolbox in order to drive change, in order to drive progress, in order to drive a roadmap, and in order to drive a P&L. And treat it no differently than a tool in the toolbox. Use it appropriately. And if you're going to use it, use it well and use it…”