Andrew Proctor

VP of IT Operations at OpenVPN

Technology operations executive specializing in multi-region SaaS infrastructure, reliability, organizational scaling, and the controlled use of AI agents.

I started in customer support, building servers and solving problems directly with customers. Over a 17-year career, I went on to establish OpenVPN’s technical operations function, hire and develop specialist teams, and take responsibility for infrastructure and product operations. Today, that work also includes leading an AI Platform team.

I designed the deployment architecture used for our cloud service’s first production launch in 2020, including the hosting, virtualization, networking, and release approach. I continue to oversee infrastructure and operations for our cloud service and self-hosted VPN software, and remain involved in architecture decisions and production incident response. The cloud service now spans more than 30 regions.

My responsibilities extend to staffing, budgets, vendor negotiations, company systems, and security and compliance oversight. I’ve also held responsibility for business intelligence and company-wide reporting, and worked with leaders across engineering, product, finance, and marketing on pricing, releases, and other business decisions.

My applied AI work builds on that operational experience. I develop agent workflows for service-desk and infrastructure teams, connecting them to the company systems needed to check requests and investigate incidents. That means deciding what context agents need, what they can reliably check, and where human approval remains necessary.