Senior Support Engineer

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.

• 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

• 5+ years of enterprise technical support experience in complex, distributed systems environments
• Expert-level diagnostic skills including:
• System and application log analysis
• Performance troubleshooting and profiling
• Network diagnostics (packet analysis, latency troubleshooting)
• API and integration troubleshooting
• Proven track record of handling critical escalations and reducing resolution times
• Understanding of distributed systems, microservices architectures, and API integrations
• Excellent communication skills - ability to explain complex technical issues to both technical and non-technical audiences
• Familiarity 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 code
• Mentorship experience - demonstrated success in upskilling technical teams

• 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 requirements
• Python familiarity - Ability to read and understand Python code for diagnostic purposes
• Process improvement mindset - Track record of implementing scalable support processes
• Data-driven approach - Experience using metrics to drive support improvements
• Crisis management - Proven ability to lead during high-pressure customer escalations

• Competitive compensation aligned with senior support engineering market rates
• Equity participation: Employee Stock Options
• Health benefits: Comprehensive medical, dental, and vision insurance
• Time off: Generous leave policies and paid company holidays
• Impact: Direct influence on support strategy and team development

Growth: Opportunity to build and lead as we scale