About Richard Genthner

I’m a security leader and infrastructure architect with roots in open source going back to 1996. I’ve spent my career building and scaling systems—from startups to platforms handling 100 million monthly active users.

What I Do Now

As VP of Infrastructure & Security and CISO at Boost Insurance, I oversee company-wide security practices, compliance initiatives, and the DevOps engineering team. I’ve spearheaded our SOC 2 Type 2 and NYS DFS Part 500 certifications, built procurement and risk assessment practices, and driven tooling decisions across the organization.

I’m currently managing 50+ security initiatives while ensuring we maintain development velocity. Security shouldn’t slow you down—it should be built into how you work.

Technical Philosophy

Infrastructure should be maintainable, scalable, and secure by default.

I focus on:

• Cloud-native architecture — Kubernetes, containers, multi-cloud deployments
• Infrastructure as Code — Pulumi, Terraform, GitOps workflows
• Security as enablement — Compliance frameworks that don’t kill productivity
• Open source first — Contributing back to the community that shaped my career

The Journey

My path through tech has been anything but conventional:

MakerBot Industries — Migrated from AWS to GCP with less than 6 hours downtime and cut cloud costs by 78%. Built multi-cloud Kubernetes with edge deployments for IoT devices. Transformed the team from shipping every 14 days to multiple deployments daily.

Poloniex — Managed global SRE operations for a major cryptocurrency exchange. Led the AWS region migration and standardized tooling for easier hiring.

US Government — Built AWS GovCloud infrastructure for federal clients through Oddball.

Symplicity — Six years managing datacenter infrastructure, including a custom VoIP system that was used for POTUS fax processing.

Open Source Roots

I’ve been contributing to open source since 1996. Started writing FreeBSD ports, got involved in various projects over the years, and continue to believe that open source is the best way to build software. Check out my GitHub for current projects.

Beyond Work

When I’m not securing infrastructure, you’ll find me involved in my local community in Maine—including volunteering as a firefighter. I’m also into cryptography, the board game Go, and exploring the intersection of philosophy and technology.

Let’s Connect

I’m always interested in discussing cloud security, compliance strategies, or interesting technical challenges. Reach out at richard@guthnur.net or connect on LinkedIn.