Director of Cloud Engineering [Remote]

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

What You'll Do

• Own Cloud Strategy & Architecture: Define the multi-year roadmap for OpenLoop's cloud platform (primarily AWS), including account structure, networking, compute, data, and disaster recovery. Make final calls on platform standards and technology trade-offs.

• Build & Lead the Team: Hire, develop, and lead cloud and infrastructure engineers and managers. Set clear expectations, grow technical leaders, and build a culture of ownership and operational rigor.

• Infrastructure as Code & Automation: Drive consistent, repeatable infrastructure using Terraform (or equivalent), CI/CD, and self-service tooling so product teams can ship quickly and safely.

• Security & Compliance by Design: Partner with Security and Compliance to embed HIPAA, SOC 2, and HITRUST controls into the platform: identity and access, encryption, logging, audit readiness, and vulnerability management.

• Reliability & Observability: Set SLOs, monitoring, and incident response standards with SRE. Own capacity planning, resilience, and backup/recovery for systems that support patient care.

• Cost Management (FinOps): Own cloud spend visibility and optimization. Build forecasting, tagging, and accountability so cost scales with the business, not ahead of it.

• Cross-Functional Leadership: Translate infrastructure constraints into clear options for Product, Engineering, Security, and Finance leaders. Support platform needs across OpenLoop and its subsidiaries.

Who You Are

• 10+ years in infrastructure, cloud, or platform engineering, with 4+ years leading engineering teams (including managers of managers preferred).

• Deep, hands-on experience architecting and operating production workloads in AWS; experience with GCP or Azure is a plus.

• Strong command of infrastructure as code (Terraform), containers and orchestration (Docker, Kubernetes/EKS, ECS), and CI/CD.

• Proven track record of improving reliability, security posture, and cloud cost efficiency at scale.

• Experience operating in regulated environments (HIPAA, SOC 2, HITRUST, PCI, or similar).

• Clear communicator who can set direction, explain the why, and influence executives and engineers alike.

Preferred

• Healthcare or health tech experience, including systems that handle PHI.

• Experience leading cloud migrations, account/landing-zone redesigns, or platform consolidation after acquisitions.

• Familiarity with AI/ML infrastructure (GPU workloads, model hosting, data pipelines).

• AWS Professional-level certifications or equivalent.

WHY YOU'LL LOVE IT:

• High Ownership: Own the platform that every OpenLoop product and client depends on.

• Real Impact: Your work directly supports clinicians and patients receiving care across the country.

• Build the Org: Shape the team, standards, and culture of cloud engineering as we scale.

• Remote Flexibility: Work from anywhere in the U.S., with collaboration anchored around Central time.

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans

• Flexible Spending/Health Savings Accounts

• Flexible PTO

• 401(k) + Company Match

• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.