This is a growing collection of my musings and thoughts on my path as an engineering leader and hobbyist. I’ve grown a lot in the last 15+ years, and not everything here is my current state of thinking. Hopefully it’s useful to you wherever you are on your own journey as a software engineer, a leader, or enthusiastic observer.

Today, I’m taking a break to recharge after a decade of building products and engineering teams in New York, San Francisco, and worldwide. If you’re here wondering if I’d like to work with you or buy something, I’m not interested right now. 🏖️

Vanta

For four years, I was Vanta’s first Head of Engineering, securing the internet and protecting consumer data, one business at a time. I’m so proud of the products, the team, and the culture we built together. During my tenure, we grew from:

  • ~$2M in annual recurring revenue to ~$110M
  • 1 product to 3
  • 6 in Software Engineering to ~120
  • 25 Vanta’ns to ~460

My time at Vanta was absolutely bananas and, so far, the highlight of my career. I’m grateful for everyone that took the leap of faith to join Vanta’s Engineering team, and I wouldn’t trade the experience for anything.

Dropbox

I spent six years at Dropbox forged in a crucible of engineering leadership. In the first five years, I cofounded Dropbox NYC and served as its site lead, overseeing growth from 0 to 160 Dropboxers with 90 engineers responsible for mission-critical products and infrastructure. I worked with an incredible group of people building the cultural and technical foundation for Dropbox’s first engineering presence outside of headquarters, and it was an amazing experience.

In my last year at Dropbox, I moved to San Francisco and led our Application Platform group, which was responsible for essential contributions to a number of major releases that year.

Early career

Before Dropbox, I cofounded Nebula Labs with Christina. We built Hoot, an Android video messaging app, and a few other things – Hoot was the first mobile app for both of us, and, as with any new technology, the victories were as glorious as the impasses were frustrating. Our learnings from building products and working together lasted much longer than what we built.

At Hunch, I led the team responsible for implementing Hunch’s recommendation algorithms on eBay’s infrastructure post-acquisition and had my first taste of getting things done at a large organization with a lot of technical debt.

I started my career at Meebo and was for whatever reason entrusted with designing and building a dynamically-optimizing adserver serving traffic for 200M+ MAUs, a big number at the time. Practical AI before it was all the rage!

At Stanford, I studied computer science and left with undergraduate and master’s degrees. I did my best to exhaust the course catalogue’s supply of systems courses, though I may have left a few behind.

As an individual contributor, much of my work has been in infrastructure and machine learning, architecting and building large-scale systems to make sense of lots of data. I spoke on these topics at PyCon 2011 and PyCon 2012. I’ve also explored the depths of Android development – there are some interesting fish at the bottom of that sea.


I’m grateful for everything I’ve learned from talented, kind mentors and learned with amazing sparring partners sharing my journey, and I’m honored to pay it forward as a formal advisor for a handful of companies and informal advisor for dozens more.

Enjoy your stay! If you’d like to get in touch, I’d love to hear from you – my contact info is very guessable.