whoami
Richard Genthner
Building Secure, Scalable Infrastructure Since 1996
Compliance & Regulatory Expertise
Recent Articles
Software Factories: Part 3 - Securing and Governing It
A software factory turns text anyone can type into code changes made by an agent with shell access. A STRIDE pass over a real one, the attacks already published against coding agents, the controls that hold, and what to tell auditors and regulators about code an agent wrote.
Software Factories: Part 2 - Building One
Inside a two-week R&D software factory: the architecture, the one principle that holds it together, five controls that reported success while doing nothing, and a single run followed from ticket to pull request.
Software Factories: Part 1 - The Idea and the Evidence
Every AI coding vendor now promises a software factory: a ticket goes in, a pull request comes out. I built one to find out what that promise is worth. Part 1 covers where the idea came from, what the 2026 wave actually is, what the evidence says, and what it cost us.
Open Source Projects
Contributing to open source since 1996 — from FreeBSD ports to cloud-native tooling
View all on GitHubCareer Journey
Boost Insurance
VP of Infrastructure & Security / CISO
2021 – Present
- Overseeing 50+ security initiatives as Chief Information Security Officer
- Spearheaded SOC 2 Type 2 and NYS DFS Part 500 compliance
- Built procurement and risk assessment practices adopted company-wide
- Migrated infrastructure from Terraform to Pulumi
- Led DevOps team and IT services operations
Poloniex
Senior Staff Engineering Manager, SRE
2021
- Managed global SRE team operations
- Led AWS US-East to EU-West migration
- Supported blockchain infrastructure across AWS ecosystem
MakerBot Industries
Director of DevOps Engineering
2017 – 2020
- Migrated AWS to GCP with <6 hours downtime, reduced costs 78%
- Implemented multi-cloud Kubernetes with edge deployments
- Transformed from 14-day releases to multiple daily deployments
- Led IoT infrastructure modernization
When I Work
Senior DevOps Engineer
2016 – 2017
- Migrated infrastructure from Linode to AWS
- Implemented Kubernetes in AWS environment
- Managed MariaDB Galera clusters across Multi-AZ/Multi-Region
Symplicity
Senior Systems Administrator
2009 – 2015
- Managed datacenter infrastructure and SAN configurations
- Built custom VoIP system used for POTUS fax processing
- Deployed configuration management with Puppet/Chef/Salt
US Government (via Oddball)
Lead DevOps Engineer
2020 – 2021
- Built AWS GovCloud infrastructure for federal clients