A while back, I kicked off a three-part series on how we built an AI-powered Chief of Staff for engineering leaders—a product that scaled to 10,000 users and later became the foundation of Outropy . The first article covered the back-end architecture powering our AI agents . In this second installment, let’s explore inference pipelines—the beating heart of any AI system, agentic or not—through the…
I love making fun of thought leaders, investors, and other folks who have no idea how software is built and operated—yet keep proclaiming that the software developer is dead. Every week, there’s at least one of these sprees on LinkedIn or in newsletters, where they go on and on about how some announcement is a game-changer that just wiped out an entire industry—from the Devin fiasco to breathless…
In 2023, we launched an AI-powered Chief of Staff for engineering leaders—an assistant that unified information across team tools and tracked critical project developments. Within a year, we attracted 10,000 users, outperforming even deep-pocketed incumbents such as Salesforce and Slack AI . Here is an early demo: By May 2024, we realized something interesting: while our AI assistant was gaining…
I just saw this article on The Verge : Let me start by saying that I am not a fan of chatbots as the primary user interface for enterprise systems. Although LLM-backed tools are significantly better at detecting intent and making data more useful, as a survivor of the fever dream that was Chatops in the mid-2010s, I don’t see how they solve any of the fundamental issues we faced with the previous…
As I dive deeper into the current renaissance of Artificial Intelligence for a project I’m working on (more on that at the end), I find myself revisiting research on how to process and make sense of information at scale. Discussions about managing large-scale information naturally remind me of the challenges engineering managers and directors face. They must navigate both information overload and…
A few months ago, I left SeatGeek without much of a plan of what to do next. My green card was finally issued in 2021, which means that I didn’t have to scramble to find a new job in forty days. For the first time in the fifteen years I have lived abroad, I could finally take my time without fear of getting on the bad side of immigration authorities. As someone who has been on a work visa for the…
Recently I sent a memo to my teams at SeatGeek setting the scene around changes that I want to see in our OKR and planning processes. I’ve asked a few people from my professional network for feedback on this email, and it seems like this is something many other organizations struggle with. I am publishing a lightly-edited version of the memo below. Hopefully, it will be useful to some people…
Just like almost anything else in software engineering, we don’t have a precise definition for the term microservice. This lack of formality doesn’t make the term worthless, however. There are a few useful characteristics we can infer whenever someone says they have an architecture that follows this paradigm. One such characteristic of “microservices-based architecture” is that they have a lot of…
The Back-end for Front-end (BFF) Pattern was originated at SoundCloud. It takes its name from the internal framework we built to make application-specific APIs easier to write and maintain. Since then, it has taken a life of its own, with various articles, books, and open source software that teach, discuss, or implement it. More recently, another approach to API architecture and design comes in…
Maybe you are a new engineering leader at red-hot startup . The founders hired you on account of your previous experience at a successful tech company, they brought you in to take engineering to the next level. After a few weeks of onboarding, you now have a list of changes you want to implement. How do you find a way to propose that without making the old guard feel alienated from the process? Or…