At one point in 2019, several parts of Stripe’s engineering organization were going through a polite civil war. The conflict was driven by one group’s belief that Java should replace Ruby. Java would, they posited, address the ongoing challenge of delivering a quality platform in the face of both a rapidly growing business and a rapidly growing engineering organization. The other group believed Stripe’s problems were driven by a product domain with high essential complexity and numerous, demanding external partners ranging from users to financial institutions to governments; switching programm ..read more

I’ve been reading Steven Sinofsky’s Hardcore Software, and particularly enjoyed this quote from a memo discussed in the Zero Defects chapter: You can improve the quality of your code, and if you do, the rewards for yourself and for Microsoft will be immense. The hardest part is to decide that you want to write perfect code. If I wrote that in an internal memo, I imagine the engineering team would mutiny, but software quality is certainly an interesting topic where I continue to refine my thinking. There are so many software quality playbooks out there, and I increasingly believe that all the ..read more

A month ago, I wrote up some notes on using LLMs in your product, and yesterday I got to present an iteration on those notes to the folks at the Sapphire Venture’s 2024 Hypergrowth Engineering Summit. If you’re interested, you can watch a recording of my talk on Youtube. There’s a lot of overlap with the notes, but I also go into Carta’s approach thus-far to incorporating LLMs into our product. (Note that it’s a recording of a practice run I did earlier in the week, not a recording from the venue itself, so it’s definitely amateur quality but the content is still all there ..read more

Some governmental agencies have started to adopt No Wrong Door policies, which aim to provide help–often health or mental health services–to individuals even if they show up to the wrong agency to request help. The core insight is that the employees at those agencies are far better equipped to navigate their own bureaucracies than an individual who knows nothing about the bureaucracy’s internal function. For the most part, technology organizations are not complex bureaucracies, but sometimes they do seem to operate that way. A particularly common pattern is along the lines of: Product Enginee ..read more

Whether you’re a product engineer, a product manager, or an engineering executive, you’ve probably been pushed to consider using Large Language Models (LLM) to extend your product or enhance your processes. 2023-2024 is an interesting era for LLM adoption, where these capabilities have transitioned into the mainstream, with many companies worrying that they’re falling behind despite the fact that most integrations appear superficial. That context makes LLM adoption a great topic for a strategy case study. This document is an engineering strategy document determining how a hypothetical company ..read more

One of the common conceits in leadership is that nobody is truly essential for a company’s continuity. I call it a conceit, but I do mostly agree with it: I’ve felt literally sick after hearing about some peer’s unexpected departure, but I’m continually amazed at how resilient companies are to departures, even of important people. About two-thirds of Digg’s team left in layoffs in 2010, but we found ways to amble on. Much of Uber’s leadership team turned over in the 2017 era, and it was chaotic, but they continued on. However, even if organizations are too resilient to collapse from departures ..read more

Back when I was managing at Digg and Uber, I spent a lot of time delivering feedback to my management chain about issues in our organization. My intentions were good, but I alienated my management chain without accomplishing much. I also shared my concerns with my team, which I thought would help them understand the organization, but mostly isolated them in a Values Oasis or demoralized them instead. Those experiences taught me that pushing your organization to improve is essential leadership work, but organizations can only absorb so much improvement at a given time before they reject the per ..read more

Pretty much every company I know is looking for a way to benefit from Large Language Models. Even if their executives don’t see much applicability, their investors likely do, so they’re staring at the blank page nervously trying to come up with an idea. It’s straightforward to make an argument for LLMs improving internal efficiency somehow, but it’s much harder to describe a believable way that LLMs will make your product more useful to your customers. I’ve been working fairly directly on meaningful applicability of LLMs to existing products for the last year, and wanted to type up some semi-d ..read more

One of the most interesting questions I got after joining Calm in 2020 was whether Calm was a technology company. Most interestingly, this question wasn’t coming from friends or random strangers on the internet, it was coming from the engineers working there! In an attempt to answer those questions, I wrote up some notes, which summarize two perspectives on “being a technology company.” The first perspective is Ben Thompson’s “Software has zero marginal costs.” You’re a technology company if adding your next user doesn’t create more costs to support that user. Yes, it’s not really zero, e.g. S ..read more

At a recent offsite with Carta’s Navigators, we landed on an interesting topic: leadership roles sometimes mean that making progress on a professional initiative requires taking some personal risk. This lesson was hammered into me a decade ago during my time at Uber, where I kicked off the Uber SRE group and architectured Uber’s self-service service provisioning strategy that defined Uber’s approach to software development (which spawned a thousand thought pieces, not all complimentary). I did both without top-down approval, and made damn sure they worked out. It wasn’t that I was an anarchist ..read more