Hi, I’m Esther Olatunde, a software engineer and product-minded builder.
I started a company straight out of school (Tress, YC W17) and have been building ever since. The work I love most sits at the intersection of systems thinking, product instinct, and design sensibility. I care about the whole picture: how the system performs at 0 and at scale, how the user feels, and whether the thing we’re building actually matters.
Right now, I’m building a new company at the intersection of AI and the messy, high-stakes operational work (regulated, human-in-the-loop) that runs real businesses: the parts where demos don’t survive contact with reality. Stealth-ish, more soon.
Before that, I spent five years at Intercom, most recently leading Knowledge Foundations for Fin.ai, after earlier years shipping 0-to-1 customer engagement products and working deep in distributed systems, infrastructure, and APIs, the kind of problems where a millisecond matters and a bad abstraction haunts you for years.
I also chip in teeny angel checks alongside friends through HoaQ, backing startups in Africa and ones targeting African or diaspora markets (notably Mono, LemFi, and Renatural).
Outside of work, I’m a trained yoga instructor. It’s the one place where my brain finally stops optimizing. Curiosity is probably the thread that connects everything I do, whether I’m digging into Ruby internals, working through Cryptopals, exploring how LLMs actually work under the hood, or holding a pose I couldn’t do six months ago. I once built a simple HTTP server from scratch because it sounded like fun, and somehow ended up giving a RubyConf talk about it. I’m currently learning Irish, French, and Japanese. At the same time. 😅
If you’re building something ambitious, especially in applied AI, infra, or anything that breaks in interesting ways at scale, I’d love to talk.
This blog is an attempt at documenting my thoughts, learnings, and journey in a semi-formal, semi-consistent form.