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Remote, Oregon, United States
Remote only
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.
We're building the IT organization from the ground up at OpenLoop Health, a fast-growing telehealth platform scaling our AI-powered care delivery across digital health, brick-and-mortar, and enterprise segments. As Director of IT Operations, you'll lead the operational backbone of our infrastructure designing and scaling systems that reliably support thousands of concurrent patients, clinicians, and partners while maintaining the security and compliance standards required in healthcare.
This is a high-leverage role reporting directly to the VP of Enterprise Technology. You'll build and lead a team of 11 engineers and operators focused on infrastructure reliability, incident response, and leveraging AI to transform IT operations (automation, predictive monitoring, intelligent alerting, and beyond). You'll own IT operations strategy and be instrumental in shaping how AI improves our operational efficiency, reliability, and decision-making.
IT Operations & Infrastructure
Lead a team of 10+ global resources focused on help desk services, facility management, SOC policy enforcement, and asset management
Design and oversee infrastructure architecture for 99.5%+ uptime in a healthcare SaaS environment
Deliver a helpdesk service to maintain a 95% SLA within the response and resolution framework
Co-own incident management, escalation protocols, and post-incident review culture
Manage infrastructure spend and cloud resource optimization (AWS, GCP, or multi-cloud)
Lead technical standardization across development, security, and product teams
AI-Enhanced Operations
Identify and implement AI/ML tools to improve operational efficiency (predictive alerting, anomaly detection, root-cause analysis)
Experiment with AI-driven automation for routine operational tasks
Work with OpenLoop's AI Program to understand how AI can transform IT operations and share learnings
Build a culture of intelligent observability—moving from reactive to predictive operations
Evaluate emerging AI/ML tooling for infrastructure, monitoring, and incident response
AI Program Operations Support
Work alongside the VP of Enterprise Technology to operationalize the AI Program
Define operational requirements for AI model deployment, monitoring, and governance
Establish observability and alerting standards for AI systems at scale
Build operational runbooks and playbooks that enable safe, rapid experimentation
Security & Compliance
Partner with Security to ensure operational practices support SOC 2, HIPAA, and state healthcare compliance
Manage access control, secrets management, and least-privilege architectures
Own disaster recovery and business continuity planning
Lead quarterly compliance audits and remediation workflows
Reliability & Performance
Establish SLAs/SLOs for critical services and own performance against them
Build a culture of blameless postmortems and continuous improvement
Design monitoring, alerting, and observability infrastructure
Lead capacity planning and infrastructure roadmap
Stakeholder Management
Communicate infrastructure health, risks, and roadmap to leadership and cross-functional teams
Support product and engineering teams with infrastructure provisioning and troubleshooting
Manage relationships with vendors and cloud providers
Mentor and develop operational staff
8+ years in IT operations, infrastructure engineering, or site reliability roles
5+ years in a leadership role managing technical teams (5+ direct reports)
Proven experience operating mission-critical SaaS or healthcare platforms
Deep expertise with cloud platforms (AWS, GCP, or Azure) and infrastructure-as-code
Strong understanding of HIPAA compliance, security baselines, and healthcare regulations
Experience designing systems for 99.5%+ uptime and handling production incidents
Track record of building strong operational cultures (automation-first, blameless postmortems, on-call excellence)
Comfortable in ambiguity—ability to build processes from scratch in a fast-growing organization
Experience building IT organizations in early-stage/hypergrowth companies
Hands-on experience with containerization (Docker, Kubernetes) and modern DevOps stacks
Background in healthcare (EMR/EHR systems, telehealth platforms, etc.)
Experience supporting machine learning or AI infrastructure at scale
Familiarity with database operations, replication, and backup/recovery strategies
Knowledge of healthcare data architecture and privacy requirements
Startup experience or consulting background
Experience evaluating or implementing AI/ML tooling for operations (predictive alerting, AIOps platforms, etc.)
Track record of using AI to improve operational efficiency or decision-making
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
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.