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Richard Genthner

Building Secure, Scalable Infrastructure Since 1996

Cloud Security & Compliance Kubernetes & Container Orchestration Multi-Cloud Architecture (AWS/GCP) DevSecOps & Infrastructure as Code Zero Trust Implementation High-Scale Systems (500M+ MAU)
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Richard Genthner
100M+ Monthly Active Users Scaled
78% Cloud Cost Reduction
50+ Security Initiatives Led
29+ Years in Tech

Compliance & Regulatory Expertise

SOC 2 Type 2
GDPR
NYS DFS Part 500
ISO 27001
CCPA

Recent Articles

Jan 16, 2026 12 min read

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.

ai security ciso defense detection threat-intelligence security-architecture risk-management
Jan 12, 2026 13 min read

AI-Assisted Penetration Testing: Weaponizing Claude, Grok, and Metasploit - Part 2: Vulnerability Discovery & Exploitation

Moving from reconnaissance to active exploitation. A hands-on guide to using AI with Metasploit and open-source tools for authorized penetration testing.

ai security pentesting metasploit exploitation vulnerability-scanning claude grok burp-suite
Jan 8, 2026 11 min read

AI-Assisted Penetration Testing: Weaponizing Claude, Grok, and Metasploit - Part 1: OSINT & Reconnaissance

A CISO's guide to understanding how attackers leverage AI and open-source tools for reconnaissance. Part 1 of a 3-part series on AI-assisted offensive security.

ai security pentesting metasploit osint reconnaissance claude grok threat-intelligence
View all articles

Open Source Projects

Contributing to open source since 1996 — from FreeBSD ports to cloud-native tooling

bell Go

No description

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prometheus

umbrella chart

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sendecho-client JavaScript

No description

1 0
sendecho-ui JavaScript

No description

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smuggler Go

No description

1 0
funnyfarm-cli Go

No description

1 0
View all on GitHub

Career 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