Director of Engineering, Infrastructure

Clover Health

12h•$195,000 - $270,000•Remote

About The Position

We're building the cloud infrastructure and delivery platform that one of healthcare's most ambitious technology transformations runs on, and we need an Engineering Director to own the Infrastructure behind it all. This is a player-coach role where you'll lead strategy and stay hands-on in the work alongside a small, focused team, reporting directly to the CTO. This role is about infrastructure and developer enablement. As our AI strategy evolves, we see a world where many outside of traditional engineering and data roles will contribute to our technology ecosystem. We believe reliability, security, and cost discipline come from good platform design and automation, and that ticket queues and runbooks are signs we haven't solved the underlying problem. You'll bring a clear point of view on what a modern, AI-native infrastructure org should look like, the judgment and technical skill to make it real, and the leadership instincts to build and develop the contributors around you.

Requirements

An engineering background with deep, hands-on experience operating production infrastructure across at least two major clouds (GCP, AWS, Azure) and with modern infrastructure-as-code (Terraform or similar)
Built and operated modern CI/CD systems, dev environments, and observability stacks. What you've shipped matters more than the size of the fleet you've managed.
Built and operated infrastructure across different company sizes and business contexts. Cross-domain breadth is a real asset; experience in regulated domains (healthcare, financial services) is helpful but not required
Hold a strong, well-reasoned point of view on platform philosophy, and can defend when to standardize, when to give teams room, and how to make the safe path the easy path
Shipped AI-native operational systems. That might be AI agents that triage alerts, draft RCAs, manage cost, or execute runbooks, or frameworks that let non-traditional contributors (junior engineers, analysts, AI agents, vibe-coders) ship safely.
Action-oriented on governance and security participation. You document what matters, automate what you can, and don't let process become a bottleneck
Built and developed teams. You think about composition intentionally, hire for gaps, and invest in people's growth
A strong communicator: clear, direct, and concise with both technical and non-technical audiences

Nice To Haves

Experience in regulated domains (healthcare, financial services)

Responsibilities

Own cloud infrastructure end-to-end across our cloud environments, staying hands-on with IaC, CI/CD, and observability alongside the team
Own the SDLC surface area (dev environments, lower envs, release mechanics, monitoring and response) so engineers can ship in minutes rather than days
Build the substrate that lets AI agents observe, reason, and act on business systems with safe defaults, and the rails that let AI-assisted apps from people outside of tech be deployed and supported without becoming operational liabilities
Participate in security operations alongside our SecOps team on CSPM, threat management, and patch management as the infrastructure-side owner of remediations
Frame infrastructure decisions in terms of business outcomes (operational efficiency, financial impact, clinical results), and make progress and tradeoffs visible to leadership as a natural byproduct of how you work
Lead and develop a small, high-impact team, and operate as a peer to our SecOps, Data, IT Systems, and App Engineering leaders as a unifying technical force across the org