Job Description
Description
OpenVPN is building out AI tooling across the organization, but the infrastructure, governance, and
operational patterns around it don’t exist yet. This is a greenfield ownership role. You won’t be inheriting
a playbook — you’ll be writing it. You’ll define the architectural standards, establish the governance
frameworks, and build the platform layer from the ground up: developer tooling, internal AI-powered
workflows, and the cloud infrastructure (Vertex AI, etc.) that supports it all. If it touches AI at OpenVPN, it
runs through you.
What You’ll Own
AI Developer Tooling & Enablement
• Own the rollout and operational management of AI-assisted development tools across engineering
(e.g., Cursor, Copilot, Claude Code)
• Define and implement access controls, license management, and usage policies that satisfy
SOC2/ISO 27001 requirements
• Build cost tracking and reporting so leadership has visibility into AI tool spend and usage patterns
across the org
• Reduce friction for engineers adopting these tools while maintaining security and auditability
Internal AI-Powered Workflows
• Partner with teams across the org to identify, build, and support internal AI applications such as
RAG pipelines, agents, and automation workflows
• Evaluate and recommend tooling, frameworks, and patterns based on what teams actually need
• Define where IaaS’s responsibility ends and consuming teams’ begins – this boundary doesn’t
exist yet; you’ll help draw it
Governance, Security & Compliance
• Advise on data governance policies for LLM usage, including what data can go into which models,
where outputs are stored, and how audit trails are maintained
• Ensure AI infrastructure and tooling meets existing SOC2 and ISO 27001 controls and can be
evidenced in audits
• Provide leadership with clear, regular reporting on AI adoption, cost, risk, and usage across the
org
AI/ML Cloud Infrastructure
• Stand up and manage AI/ML infrastructure, primarily on GCP (Vertex AI) within OpenVPN’s
existing environment
• Design the Terraform modules and IaC patterns for AI infrastructure that follow the team’s existing
conventions (e.g., Atlantis-driven GitOps workflows)
Cost Management
• Build visibility into AI/ML infrastructure costs and implement controls (spot instances, auto-scaling
policies, idle resource cleanup) consistent with how compute costs are managed elsewhere
• Evaluate build-vs-buy decisions for AI/ML infrastructure components and managed services with
an eye toward operational fit within existing patterns
Requirements
Must Have
✓ Hands-on experience standing up and managing AI/ML infrastructure such as Vertex AI, or
comparable platforms (SageMaker, Azure ML)
✓ Has set up AI developer tooling (Cursor, Copilot, etc.) at an org level, including managing
rollout, access, and cost
✓ Infrastructure-as-code fluency: Terraform is our primary tool, managed through Atlantis. You
should be able to write modules that other teams consume through self-service
✓ Ability to work across teams and define boundaries for a new capability area that doesn’t
have established patterns yet
✓ Can communicate clearly with leadership about cost, risk, and value of AI investments
Strong Preference
• Strong GCP experience
• Understanding of security and compliance in a regulated environment (SOC2, ISO 27001);
experience implementing controls or working within audit frameworks
• Platform engineering mindset: thinks about how to make things self-service, auditable, and
repeatable rather than one-off
• Experience with model serving infrastructure: managed inference services (Vertex AI endpoints,
Bedrock, Azure OpenAI) or self-hosted frameworks, including routing, scaling, monitoring, and cost
controls
• Experience with RAG infrastructure components such as vector databases, embedding pipelines,
and retrieval systems
• Familiarity with LLM operational patterns including prompt caching, batching strategies, model
versioning, and monitoring/observability approaches specific to inference workloads
Nice to Have
• Familiarity with Kubernetes/EKS since the rest of the team’s infra lives there
• Experience with data infrastructure (BigQuery, Kafka, Cloud Composer)
• Configuration management experience with Ansible or Puppet
• Familiarity with AI/ML managed services on AWS (Bedrock, SageMaker) and how they fit
alongside self-managed infrastructure
• Has gone through an ownership transition or greenfield buildout before and knows how to
establish patterns from scratch without over-engineering
Our philosophy is that we are a small, closely-knit team and we care deeply about you.
What We Offer:
Competitive compensation that reflects your skills and contributions(compensation for this position will be tailored based on qualifications and experience. Candidates offered the position can expect a starting base salary between $140,000 and $150,000 per year)
Generous time off opportunities to recharge and enjoy life outside of work
Flexible scheduling to support work‑life balance
Fully remote work environment — work from anywhere you’re most productive
Global collaboration with talented colleagues in Silicon Valley and around the world
Please note that the company is unable to provide visa sponsorship for this position, either now or in the future. Candidates must be authorized to work without the need for current or future visa sponsorship.
