whoami
Richard Genthner
Building Secure, Scalable Infrastructure Since 1996
Compliance & Regulatory Expertise
Recent Articles
Threat Modeling for the Rest of Us: Part 1 - The Playbook I Wish Existed
Your auditor just asked for a threat model. Now what? A practitioner's field guide to what threat modeling actually is, which approach fits your organization, and how to run your first session in 60 minutes.
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.
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