In this monologue, Keith Rabois explains why fostering employee development is especially difficult in high‑growth startups, where the organization constantly reinvents itself to sustain 10x annual expansion. Traditional, slower-paced career training is often impossible, but the rapid change creates a flood of new challenges that can serve as on‑the‑job learning opportunities for high‑potential staff. He contrasts two growth trajectories: a relatively linear, steady expansion like LinkedIn (2003‑2012) that allows employees to grow into roles over time, versus the steep, sometimes vertical growth experienced at Square, where headcount and transaction volume can triple or ten‑fold in a year. Rabois discusses the need to align individual growth slopes with company velocity, the impracticality of maintaining a 70/30 internal‑promotion versus external‑hire ratio at extreme growth rates, and the managerial challenge of accommodating both “jump‑in‑the‑water” learners and those who prefer structured training. He also references feedback from Vinod Khosla that underscores the limits of internal promotion under such conditions.
Chapters
How employees can grow in a high growth startup is a very challenging one. The constraints of a high growth startup are very severe because the company itself is reinventing itself all of the time. When you're growing 10x a year, the organization is reinventing itself, the hiring is the team is reinventing itself. And it's very difficult to take your sort of foot off the gas and allow people time into traditional training to grow their own careers. I think the flip side of that is because everything is moving so fast and the world is changing so fast and the organization is changing so fast, there are opportunities for people to embrace that and get assigned or ask for the assignment of new challenges virtually every week. So, it's not a zero in a large organization, it's fairly stable. If I get assigned a project that's interesting, it's sort of a zero sum game. It means if I'm assigned it, someone else is not. In a high growth startup, there's so many opportunities and you can't hire new talent fast enough to manage those opportunities that there's an infinite set of possibilities for high potential people within the organization to embrace and grow and test themselves. It's a little bit like the learn to swim by jumping in the water technique. And that's really the best way in a high growth startup. That said, there are people who prefer to learn by taking swim lessons than being thrown in the water and asked not to drown. That can be challenging to manage in a high-growth startup to allow those people the comfort of growing in a system that works for them. There's a graph I like to draw about the velocity of growth of a startup or the pace of growth in a startup and the individual growth of an individual or the individual executive. And if the slope of the company line is greater than the slope of the individual line, you have to make a change in responsibilities and add someone to the team. And the problem is when the slope is vertical, which actually does happen in Silicon Valley, not that commonly, not that frequently, but when you have a true vertical startup, almost nobody can keep up with that slope. So you have to make a lot of changes constantly. In a more successful but linear slope, let's call it LinkedIn, my days of 2003 to 2012, LinkedIn was always linear. There was a lot of room for people to grow into their positions, to learn their positions, to find their ground because the company never exploded even though it turned into a very explosive company as a whole. But it was over a decade. It was a $24 billion company, but it never really had that kind of ridiculous slope. Whereas at Square, in contrast, we had years where we would triple the headcount and 10x payment volume or something like that. And the opportunities for people to learn that fast, the number of people who can actually learn that fast is very rare. So I had this whole plan of maybe recruiting 30% of leaders from outside the company and promoting 70% from within. And Vinod Khosla gave me feedback that that's completely impossible at the rate of growth that we're growing. I said, if you did your job amazingly as a manager, leader, mentor, 50-50 would be a heroic achievement. And it turned out he was right.
