whoami
Richard Genthner
Building Secure, Scalable Infrastructure Since 1996
Compliance & Regulatory Expertise
Recent Articles
AI Coding Security and Sandboxing Your Filesystem
You gave an LLM a shell. Now what? A practical guide to sandboxing AI coding agents — from filesystem isolation and permission controls to credential hygiene and organizational policy. Defense in depth for the age of agentic development.
Shadow AI and the CISO's Blind Spot: Everyone's an Engineer Now
The AI revolution didn't knock on the CISO's door — it walked right past it. I'm presenting at SecureWorld Boston in April on how cybersecurity teams must evolve to address Shadow AI, the fastest-growing unmanaged risk in the enterprise.
Meet Henry: Building a Secure, Personal Multi-AI Coding Relay with Go and Claude Code
How I built Henry — a private Telegram bot that relays coding questions to Claude, Grok, and GPT with persistent sessions, MCP integration, and a security-first architecture. A deep dive into the design, the code, and why I built it.
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