Square

“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 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 o…”

“One of the things that I'm very vocal about internally is the importance of good escalations. Like I want good escalations to come to me from all over the company, certainly folks in my purview, but also folks outside of my purview.”

“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.”

“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 i…”

“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 puz…”

“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 in a way that is effectively neutral.”

“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 every…”

“Hey, anytime I do this again, I'm going to insist on having written goals upfront.”

“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 gr…”

“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 ha…”

“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 functiona…”

“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 t…”

“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 …”

“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.”

“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…”

“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…”

“Sales is centralized. Account management is centralized. Marketing is centralized. And so you've got a set of GMs that own a P and L that own a set of products that have these teams and their remit as direct managers. And then you have central go to market tea…”

“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 liv…”

“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 appropri…”

“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.”

“Alyssa reads everything. And I mean everything. And she's not above any real piece of work and nothing is beneath her at some level. Like if there is a material, a piece of material that is being put in front of her or is in her queue, she will get to it. It m…”

“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 ea…”

“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.”

“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 …”

“We have written principles on how we want span of control to work in the context of work design, how we want ratios to work in the context of work design, and we can test against those principles, and we can measure even against those principles, and we do.”

“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 …”

“The catch on that, and like one of the tricks is just, it's very, very difficult to be able to build awareness and be able to acquire, at least at the bottom of the market, be able to acquire at an affordable CAC if you don't have really great brand awareness,…”

“So to give you an example, when Alyssa came into Square, I think we had 13 or 14 different instances of a shopping cart, of ways that people put items into some sort of cart object, and then ultimately checked out.”

“That started off the unique insight that like, hey, we kind of have a pretty good view into the revenue of a business. We don't have a full view on the business. We have a unique view on the revenue coming into a business. And so that really puts us into a pos…”

“Square Invoices grew to be our second biggest, I'm not sure where it is, Now, or if they disclose all this, but it grew to be at the point of the IPO, I think it was our second biggest payment product.”

“The majority of Square businesses are solopreneurs. They're individuals, individual sellers. And, you know, the last decade or so, I think the company's really made a successful march up market. So we've got a lot of larger businesses now, but, you know, back …”

“At Square, what we did and what the company's still doing is, is came up with a vertical strategy where we had, okay, we've got our base square point of sale out of the box, you know, works for most industries with simple needs. And as you start to get more ad…”

“If we're going to expand off the wedge, how does the wedge product, whatever the first one is, really help unlock the door to the second? What are the sort of unique insight, unique advantage or right to win? Does the first product open up for the second?”

“This can't just be like a one size fits all thing anymore. Like the differences of jobs to be done across these industries are just too stark.”

“We didn't do much of that at Square, a lot of it was kind of focused on what does the next year look like?”

“I think I learned a lot there from my days at Square, where that's kind of how Sarah and Jack talked about the IPL. It wasn't the finish line. It was just another milestone amongst many milestones.”