High Growth Handbook: Scaling Startups From 10 to 10,000 People

Early on, when we were scaling Box at 20 or 30 employees, we came to this question. And I asked myself, “Do I look like these other CEOs that have scaled big companies?” A lot of times it didn’t feel like I was like them. I focus on a very different set of things. I don’t really like all the stuff that they like to do. But I ended up realizing that

There are a lot of reasons why diversity matters, and it’s important for every company that’s going to invest in this—invest time, invest resources, invest energy—to have a reason that’s specific to them. The first reason is that there is a lot of research showing diverse teams are stronger when it comes to analytical thinking and complex problem-s

You should never drag out a re-org or pre-announce it. Try not to announce “this week we will re-organize product, and next month we will change engineering.” If possible, all elements of the re-org need to be communicated and implemented simultaneously. If you pre-announce a portion of the re-org, that team will not get any work done until the re-

These companies act as “feeders” to startups who are looking for experienced hires or executives who have operated at scale. Since these large companies lack a lot of diverse employees (particularly in engineering, product, and design), diversity hiring becomes more difficult for downstream startups. As a startup, you will need to look at less comm

Typically, the only real “legal” capability of a chair (depending on charter and state of incorporation) is the ability to call for a board meeting independently of the CEO (assuming the roles are split). In early-stage startups, the title “chair” is pretty meaningless; most won’t have a stand-alone chair.

The analogy I drew was to games, or sports. I said, “You know why playing a game is fun? Because it has rules, and you have a way to win. Picture a bunch of people showing up at some athletic field with random equipment and no rules. People are going to get hurt. You don’t know what you’re playing for, you don’t know how to win, you don’t know how

Hiring a COO is not about adding a title to your org chart, but rather finding the background and experience you are looking for. Optimally, you want someone who will come in to complement, operationalize, and execute your vision as a founder. Many technical or product-focused founders want to (and should) remain focused on the product and overall

Think about diversity broadly. Did you include women and underrepresented minorities as investors? How diverse is your board and executive team?

The nature of human beings is that you come into a company, you work like a dog, you work really hard, and then you get tired and hire someone to do your job. And it always takes two new hires to do your job. Just repeat that ad nauseam, and you end up with five thousand people sitting around at a web app company. And everyone from the outside is l