Join Our Mission to Revolutionize Healthcare
Thoughtful is pioneering a new approach to automation for all healthcare providers! Our AI-powered Revenue Cycle Automation platform enables the healthcare industry to automate and improve its core business operations.
We're looking for an Exceptional Principal Support Engineer to transform our support operations.
As a critical member of our support organization, you will serve as the diagnostic expert and escalation point between our Customer Support Agents and Solutions Engineers. You'll bring enterprise-level troubleshooting expertise to complex customer issues, mentor the team on diagnostic methodologies, and help us scale our support capabilities to match our rapid growth. Your work will directly impact customer satisfaction and enable healthcare organizations to operate more efficiently.
Your Role
- Diagnose : Lead comprehensive technical investigations using advanced troubleshooting methodologies (log analysis, network diagnostics, performance profiling)
- Resolve : Handle all support activities from Tier 1 through Tier 3, excluding code changes, serving as the primary escalation point for complex issues
- Mentor : Develop and train the support team on diagnostic best practices, creating playbooks and standardized troubleshooting procedures
- Collaborate : Work closely with CSAs, Solutions Engineers, and Forward Deployed Engineers to ensure smooth handoffs and efficient issue resolution
- Optimize : Identify patterns in support issues to drive process improvements and preventive measures
- Document : Create and maintain comprehensive troubleshooting guides, knowledge base articles, and root cause analyses
Your Qualifications
5+ years of enterprise technical support experience in complex, distributed systems environmentsExpert-level diagnostic skills including :System and application log analysis
Performance troubleshooting and profilingNetwork diagnostics (packet analysis, latency troubleshooting)API and integration troubleshootingProven track record of handling critical escalations and reducing resolution timesUnderstanding of distributed systems, microservices architectures, and API integrationsExcellent communication skills - ability to explain complex technical issues to both technical and non-technical audiencesFamiliarity with monitoring and observability tools (DataDog, New Relic, ELK stack, or similar)Working knowledge of scripting for automation (Python, Bash, or similar) - not required to write production codeMentorship experience - demonstrated success in upskilling technical teamsWhat Sets You Apart
Healthcare IT experience - Understanding of healthcare systems, HIPAA regulations, and healthcare data standards (HL7, FHIR)AI / ML exposure - Familiarity with AI / ML systems and their unique troubleshooting requirementsPython familiarity - Ability to read and understand Python code for diagnostic purposesProcess improvement mindset - Track record of implementing scalable support processesData-driven approach - Experience using metrics to drive support improvementsCrisis management - Proven ability to lead during high-pressure customer escalationsWhy Thoughtful?
Competitive compensation aligned with senior support engineering market ratesEquity participation : Employee Stock OptionsHealth benefits : Comprehensive medical, dental, and vision insuranceTime off : Generous leave policies and paid company holidaysImpact : Direct influence on support strategy and team developmentGrowth
Opportunity to build and lead as we scale
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