Senior Technical Support Engineer - Overnight Shift (PST)

Accountabilities: Serve as the senior technical escalation resource for complex issues involving reporting platforms, HL7 integrations, speech recognition systems, and customer Windows and PACS environments, investigating problems through to root cause. Lead responses to high-priority customer incidents (P1/P2), coordinate with Engineering on-call teams, manage customer-facing incident bridges, and deliver timely root-cause analyses and post-incident reviews. Oversee technical support for enterprise go-lives, including readiness assessments, implementation coordination, hypercare support, and transitions into ongoing operations. Improve ticket quality and service-level agreement (SLA) performance by establishing triage standards, escalation criteria, and effective workflows across Zendesk and Linear. Identify recurring support issues and collaborate with Product and Engineering teams to address underlying causes and reduce ticket volume. Develop and maintain technical runbooks, troubleshooting documentation, and Help Center resources covering products and integrations. Mentor and coach support engineers through shadowing, ticket reviews, and knowledge-sharing initiatives to improve overall team capabilities. Collaborate with automation and AI teams to design, test, and implement intelligent triage, ticket classification, and self-service tools that reduce manual workload. Represent Technical Support in engineering triage, incident reviews, and release planning, providing customer-impact insights to guide prioritization. Participate in and help lead the on-call rotation, including occasional additional night and weekend coverage, while contributing to the development of scalable 24/7 support operations. Requirements: 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. Benefits: Annual salary range of $86,000–$115,000 , depending on experience, training, geographic location, and market conditions. Comprehensive medical, dental, and vision insurance. Life insurance coverage. Health Savings Account (HSA) with employer matching. Flexible Spending Account (FSA) and Dependent Care Flexible Spending Account (DCFSA). 401(k) retirement plan. 11 paid company holidays annually. Flexible paid time off (PTO) policy. Annual company-wide offsite and periodic team offsites. Annual equipment stipend. Fully remote working arrangement for eligible candidates located anywhere in the United States. Opportunity to contribute to innovative AI solutions supporting healthcare professionals and patient care. Collaborative environment with opportunities to influence technical support processes, automation, and team development.