Avery Pennarun
Co-founder And CEO at Tailscale
Montreal, Quebec, Canada
Summary
🤩
Rockstar🎓
Top SchoolAvery Pennarun is a veteran software entrepreneur and engineer with 27 years of experience who currently leads Tailscale as co-founder and CEO, building human-scale secure networks that combine WireGuard with 2FA and centralized policy. Deeply pragmatic, he prefers turning hard problems into "boring" reliable systems, evidenced by low-level networking and systems work on WireGuard, WireGuard-go, and the widely used Tailscale project. His background spans founding multiple startups, high-availability systems engineering, and strategic technical roles at Google Fiber where he pushed the state of the art in Wi‑Fi analytics and CPE software. An active open-source contributor, he has tackled race conditions, performance bottlenecks, and stability in core networking code while also improving UX and tooling in projects like blip and bup. Based in Montreal, Avery blends founder-level product judgment with hands-on systems engineering and a knack for simplifying complex distributed systems.
27 years of coding experience
22 years of employment as a software developer
B.A.Sc. Computer Engineering, B.A.Sc. Computer Engineering at University of Waterloo
Stackoverflow
10,948reputation
1.4mreached
100answers
17questions
git
top-5%
memory-management
top-5%
git-submodules
top-5%
delphi
top-5%
linux
top-5%
Github Skills (76)
dependency-management10
python10
test-framework10
c1110
wireguard10
subprocess10
c1710
build-automation10
javascript10
jquery10
socket10
front-end-development10
html10
sh10
filtering10
Programming languages (12)
Github contributions (5)
apenwarr/bup
Oct 2009 - Aug 2012
Please switch to using the github.com/bup/bup repo instead!
Role in this project:
Back-end Developer
Back-end DeveloperContributions:527 commits in 2 years 10 months
Contributions summary:Avery primarily worked on adding new functionalities and fixing bugs for a file splitting tool. Their contributions included implementing a rolling checksum algorithm, writing C modules for performance optimization, and making modifications to ensure correct handling of file boundaries and various edge cases. The user also focused on integrating with Git and creating a command-line interface to interact with the repository. They demonstrated a strong grasp of core system concepts for efficient file handling.
switch
apenwarr/redo
Nov 2010 - Jul 2021
Smaller, easier, more powerful, and more reliable than make. An implementation of djb's redo.
Role in this project:Backend Developer & Automation Engineer
Backend Developer & Automation EngineerContributions:1 review, 500 commits, 37 PRs in 10 years 10 months
Contributions summary:Avery primarily focused on implementing core features and improving the build process for the `redo` project, a build automation tool. They added crucial dependency checking, along with a -v option for verbose output and a -x option for command tracing. The user also integrated a job server (jwack) to handle parallel builds, enhancing the efficiency of the build process, and designed and integrated an automatic documentation generator system.
smallerparallelreliablemakefileredo
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