Senior Technical Support Engineer - Overnight Shift (PST)

Take on a key technical leadership role supporting innovative AI-powered healthcare technology used by radiology teams and healthcare organizations. As a senior escalation point, you will resolve complex enterprise support challenges across clinical software, integrations, and customer IT environments. You will take ownership of critical incidents, guide customers through high-impact technical issues, and collaborate closely with Engineering, Product, and Implementation teams. Beyond resolving problems, you will help strengthen support operations through better processes, automation, documentation, and mentoring. This is an opportunity to make a meaningful contribution to technology that supports physicians and improves patient care. The position is fully remote and follows a Wednesday-to-Saturday overnight schedule aligned with Pacific Time.

• 6+ years of experience in customer-facing technical roles, such as support engineering, technical account management, solutions engineering, or implementation engineering, supporting enterprise SaaS environments.

• At least 2 years of experience serving as a senior technical escalation resource or team lead.

• Availability to work overnight hours aligned with Pacific Standard Time, following a Wednesday-to-Saturday schedule that includes weekend coverage.

• Strong healthcare IT expertise, including hands-on experience with HL7 v2 messaging (ORU, ORM, ADT), interface engines, and PACS/RIS or clinical dictation workflows in hospital or radiology environments.

• Proven ability to troubleshoot web and desktop applications in complex Windows enterprise environments.

• Experience analyzing application logs and resolving network, VPN, single sign-on (SSO), and identity-related issues involving technologies such as SAML, Azure AD, Okta, and ADFS.

• Excellent communication skills and the ability to take ownership of customer-facing incidents while providing clear, timely updates to internal and external stakeholders.

• Experience mentoring or coaching technical support professionals and improving team performance without relying on direct management authority.

• Strong written and verbal communication skills, including the ability to work effectively with physicians, IT administrators, and executive stakeholders.

• Ability to remain composed and organized under pressure while managing a high volume of active issues.

• Adaptability and initiative in a fast-paced startup environment, with a proactive approach to documenting knowledge and building scalable processes.

• Experience with speech recognition or clinical documentation products is an advantage.

• Scripting or querying knowledge in SQL, Python, or PowerShell for log analysis, data extraction, and basic automation is a plus.

• Familiarity with workflow automation platforms such as n8n or Tray, and observability tools such as Better Stack or Datadog, is beneficial.

• Exposure to FHIR or Medplum is desirable.

• Advanced knowledge of Zendesk features, including triggers, SLAs, views, and reporting, as well as Linear or equivalent ticket management tools, is advantageous.

• Previous experience in radiology practices, teleradiology groups, healthcare software, or similar clinical technology environments is a plus.

• Experience supporting multi-site enterprise healthcare deployments or working alongside Implementation and Professional Services teams is highly desirable.