Jason Riedel

Jason Riedel

Self-taught, startup CTO, cloud infrastructure, networking, software development, husband and father of 3 boys.

In 1992, when I was 9 years old, my dad brought home our first computer and I was hooked. I started writing code at 12 and never looked back, earning my A+ certification at 16 and my CCNA at 17. I am self-taught and have spent my career building Internet Service Providers and things on the Internet ever since.

My career has tracked the evolution of cloud infrastructure pretty closely. I designed private clouds and built the data center architecture that still runs PayPal's production systems today, then moved to hybrid cloud with AWS and OpenStack at Symantec, then led PayPal's first public cloud engineering team on Google Cloud Platform. Python is my main language, though I work across the stack in Go, JavaScript, and Java as well. Linux has always been home.

In 2019 I co-founded Aspireship, a platform helping people break into tech sales careers. We scaled to 18 employees and $2M ARR. In 2023, due to rapidly rising interest rates and a budget crisis, I chose to step back from the CTO role and still advise the company today. Outside of work I prioritize time with my 3 sons, staying abreast of the latest technology, fitness, and music.


Timeline
2024
now
Head of Infrastructure Architecture

Leading a small team of director-level architects covering SRE, Developer Platforms, cloud, and AI/ML. Designing PayPal's future cell-based architecture, which is a migration away from the foundational design I originally built over a decade ago that still powers PayPal's production infrastructure today. Also serving as lead infrastructure architect for PayPal's Cloud Modernization initiative on Google Cloud Platform.

2023
2024
Head of Cyber Defense

Led a global cybersecurity operations team across the US, Singapore, and China. Owned the strategy and vision for PayPal's Cybersecurity Defense Center across all business units worldwide.

2019
now
Co-Founder & CTO (2019 to 2023), Advisor (2023 to present)

Co-founded Aspireship to help people without traditional backgrounds break into tech careers. Built the platform from scratch with Python, Flask, PostgreSQL, GraphQL, React, Docker, AWS, and GCP. Scaled to 18 employees and $2M ARR as CTO before transitioning to an advisory role I still hold today.

2018
2019
Head of Public Cloud Engineering

Stood up and led PayPal's first Public Cloud Engineering team. Served as lead architect for PayPal's inaugural Google Cloud implementation, designing the GCP architecture, security framework, IAM structures, and automated provisioning infrastructure built on Terraform.

2016
2018
Symantec
Director, Cloud Platform & Engineering

Led cloud architecture and engineering for Symantec's enterprise security products. Designed and built a hybrid cloud with AWS and OpenStack. Served as lead architect and developer in Go and Python for the Cloud Intelligence Service, a CMDB enabling automation, provisioning, and environmental consistency across the platform.

2005
2016
Senior Architect, Site Reliability Engineering

Designed the next-generation data center campus and availability zone architecture for PayPal and eBay's multi-tenant private cloud, infrastructure that has been running in production since 2012. Served as operations architect for PayPal's in-memory NoSQL datastore, the full replatforming of PayPal's payment software, and checkout and point-of-sale systems deployed at Home Depot, Radio Shack, and Babies R Us.

2004
2005
Pearson School Technology
Systems Administrator, Production Services

Administered Linux and Solaris production systems using Kickstart and Jumpstart. Owned all monitoring with Nagios and Foglight and built an internal asset tracking system in Perl and MySQL.

2001
2004
CableOne
Internet Engineer

Hybrid network and systems engineering role. Traveled to install cable modem head ends for new markets and maintained internet circuits at T1, DS3, OC3, and OC12 speeds. Troubleshot core network routing issues across EIGRP, BGP, and RIP. Managed DNS, mail servers, and web infrastructure, and wrote Perl scripts for IP reporting and network device management.

1999
2001
PSN Internet Services
Senior Systems Administrator

Most senior technical role in the company, responsible for all Unix and Linux systems and networks for dial-up and DSL service, while attending school full-time. Maintained Cisco 7204 VXR routing configuration for IP and BGP. Managed Linux, Solaris, and BSDi systems running Apache and Sendmail, and developed PHP services to provision new DSL subscribers to routers.


Highlights

Teaching
I teach infrastructure engineering and systems programming through my course ansibleclone.com and my YouTube channel. The course walks you through building Commander, a parallel SSH automation tool in the spirit of Ansible, from scratch.

Podcast Appearances
Code Story Podcast
Code Story — S4 Bonus: Jason Riedel, Aspireship (April 2021)
The Unwritten Playbook
The Unwritten Playbook — Ep. 40: People over Product (August 2021)
The Unwritten Playbook interview clip
The Unwritten Playbook — Goals effect trajectory (August 2021)

Writing
Technical writing on cloud infrastructure, DevOps, Python, and systems engineering at tuxlabs.com.

Music
I ran a hip hop label called HaveIT Music for about 8 years. Hip hop has always been a serious creative outlet alongside the technical work.
Xpoz Magazine Issue 57 — RythmIQ & HaveIT Music
Xpoz Magazine, Issue 57 — RythmIQ & HaveIT Music feature
Xpoz Magazine interview
Read the interview — Xpoz Magazine, Issue 57
Shutup & Listen Vol. 1 promo video
Shutup & Listen, Vol. 1 — Album promo video
RythmIQ promo
Hand-drawn portrait
Photo shoot
Photo shoot
With producer No ID
With Sway
With Willy Northpole
With producer 9th Wonder

Resume

Full work history covering 25 years in infrastructure, cloud architecture, and security leadership.

View Resume (PDF)