whoami
Richard Genthner
Building Secure, Scalable Infrastructure Since 1996
Compliance & Regulatory Expertise
Recent Articles
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.
OpenClaw and the Rise of Agentic Exploitation: When Autonomous AI Tools Become Security Threats
An investigation into how open agentic AI frameworks like Clawdbot and OpenClaw are reshaping the cybersecurity landscape. From automated attack chaining to prompt injection risks, we examine the emerging threats and what organizations must do to prepare.
AI-Assisted Penetration Testing: Weaponizing Claude, Grok, and Metasploit - Part 3: Defense Implications & Why CISOs Must Care
The strategic implications of AI-assisted attacks for security leaders. Detection strategies, defensive architectures, and the action items every CISO needs to address.
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