About the author
I (Ray Ashman) am a staff software engineer, weightlifter, cyclist, and trail runner living in the United States. Over roughly the last 16 years, I’ve been both a staff-level individual contributor and a people manager (up to the Director level).
My current interests are in security: product security and - more recently - agent security, along with climate tech, accessibility, and civic tech. In particular, I’m fascinated by LLMs both as a vector and as an attacker. I’m also a talented people leader, and love talking to others about the craft of authentic leadership - but I’m currently only interested in hands-on, individual contributor roles.
Some recent professional highlights#
Wistia (2022–2026)#
I joined Wistia as a Staff Engineer and the founding engineer for Record, an in-browser video recording tool for recording solo or live with teammates over WebRTC. I built the first versions while hiring the team, and we went from idea to launch in eight months.
Later, as Director of Engineering over the video player and webinars, I stayed hands-on:
- Led the design and launch of the V2 player: 30% smaller and the fastest in its market.
- Personally worked through about 150 accessibility audit findings to bring four products to WCAG 2.2 AA conformance.
- Built guardrails for agent-written code (real-browser testing and verification loops), holding reverts to one per 40 shipped PRs.
- Introduced agentic triage for our HackerOne security reports.
Stripe (2021–2022)#
As Senior Engineering Manager for API Experience, I led the design of “V2” of the internal framework Stripe engineers use to build API products. It moved from Ruby to a Java stack built on declarative code generation and halved the time for teams to get a new API into production. My team also owned core primitives Stripe customers use every day, such as API versioning.
Mailchimp (2018–2021)#
As a staff engineer, I architected and led the build of the Mailchimp Marketplace, cut list-import times by more than 70%, and rewrote core contact-data systems in some of the oldest and most valuable code at the company. I also helped build the incident command program and wrote Computers Are the Easy Part about what we learned.
Before that, I was the backend tech lead and engineering manager for the mobile teams. I designed the APIs behind the iOS and Android apps and cut our release cycle from every eight weeks to every two.
Earlier#
At CareerBuilder I led the move from a PHP monolith to an event-driven architecture, including a resume indexing pipeline that processed millions of resumes a day, and built OAuth2 single sign-on across the product suite.
Other places to find me#
Colophon#
All artwork shown on this site comes from the Art Institute of Chicago’s open access collection of public domain works. The AIC generously provides access to the collection free of charge through a very well-designed API.
The site is set in IBM Plex Sans and IBM Plex Mono and built with Hugo.