Director, IT Operations

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. About The Role 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. What You'll Do IT Operations & Infrastructure Lead a team of 10+ global resources focused on help desk services, facility management, SOC policy enforcement, and asset managementDesign and oversee infrastructure architecture for 99.5%+ uptime in a healthcare SaaS environmentDeliver a helpdesk service to maintain a 95% SLA within the response and resolution frameworkCo-own incident management, escalation protocols, and post-incident review cultureManage 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 tasksWork with OpenLoop's AI Program to understand how AI can transform IT operations and share learningsBuild a culture of intelligent observability—moving from reactive to predictive operationsEvaluate 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 ProgramDefine operational requirements for AI model deployment, monitoring, and governanceEstablish observability and alerting standards for AI systems at scaleBuild 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 complianceManage access control, secrets management, and least-privilege architecturesOwn disaster recovery and business continuity planningLead quarterly compliance audits and remediation workflows Reliability & Performance Establish SLAs/SLOs for critical services and own performance against themBuild a culture of blameless postmortems and continuous improvementDesign monitoring, alerting, and observability infrastructureLead capacity planning and infrastructure roadmap Stakeholder Management Communicate infrastructure health, risks, and roadmap to leadership and cross-functional teamsSupport product and engineering teams with infrastructure provisioning and troubleshootingManage relationships with vendors and cloud providersMentor and develop operational staff Required Who You Are 8+ years in IT operations, infrastructure engineering, or site reliability roles5+ years in a leadership role managing technical teams (5+ direct reports)Proven experience operating mission-critical SaaS or healthcare platformsDeep expertise with cloud platforms (AWS, GCP, or Azure) and infrastructure-as-codeStrong understanding of HIPAA compliance, security baselines, and healthcare regulationsExperience designing systems for 99.5%+ uptime and handling production incidentsTrack 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 Preferred Experience building IT organizations in early-stage/hypergrowth companiesHands-on experience with containerization (Docker, Kubernetes) and modern DevOps stacksBackground in healthcare (EMR/EHR systems, telehealth platforms, etc.)Experience supporting machine learning or AI infrastructure at scaleFamiliarity with database operations, replication, and backup/recovery strategiesKnowledge of healthcare data architecture and privacy requirementsStartup experience or consulting backgroundExperience 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 Our Benefits In addition, for salaried positions you would also be eligible for: Medical, Dental, and Vision plansFlexible Spending/Health Savings AccountsFlexible PTO401(k) + Company MatchLife 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.