Department: Customer Success - Tech Support
Reports to: Manager, Technical Support
Location: Orlando - Hybrid/ 4 days at OneRail HQ/1 day remote
FLSA Status: Exempt (Salary)

Overview
OneRail is seeking a highly motivated and experienced Technical Support Lead to help drive the day-to-day success of our Technical Support team as we continue scaling our fast-growing logistics technology platform. This is a hands-on technical leadership role focused on advanced troubleshooting, team mentorship, and continuous improvement rather than formal people management. The Technical Support Lead serves as the primary escalation point for complex issues, provides day-to-day guidance to team members, and helps improve the overall effectiveness of the support function through stronger processes, documentation, and tooling.
This role exists to strengthen technical support operations as the business grows by improving issue resolution quality, enabling the team to work more efficiently, and partnering cross-functionally to address recurring platform and customer-impacting issues. The ideal candidate is a proactive, technically strong problem-solver who enjoys mentoring others, taking ownership of complex challenges, and turning ideas into action. This position plays a key role within the Technical Support department and works closely with Product, Engineering, and IT to improve customer experience and platform stability.

Responsibilities
• Serve as the primary technical escalation point for complex, high-impact support issues
• Troubleshoot advanced issues across systems, software, integrations, and platform functionality
• Own complex support cases through resolution, ensuring timely follow-up and clear communication throughout the issue lifecycle
• Provide day-to-day guidance, technical support, and knowledge sharing to team members
• Mentor team members on troubleshooting techniques, best practices, and effective customer communication
• Partner with Product, Engineering, and IT to investigate issues, identify root causes, and implement long-term solutions
• Analyze recurring support trends and identify opportunities to improve workflows, tooling, documentation, and team processes
• Develop, maintain, and improve internal SOPs, troubleshooting guides, and knowledge base documentation
• Help define and reinforce standards for triage, escalation handling, and issue resolution quality
• Support customer interactions across phone, chat, email, and other channels as needed
• Drive practical process improvements that enhance team performance and customer experience
• Perform other related duties as assigned

Qualifications
• 3+ years of experience in technical support, IT support, or a similar technical customer-facing role
• Demonstrated experience serving as a senior team resource, technical escalation point, mentor, or informal lead
• Experience troubleshooting complex systems, software applications, integrations, and customer-impacting issues
• Experience working with REST APIs
• Strong analytical and problem-solving skills with a proactive, ownership-driven mindset
• Excellent written and verbal communication skills
• Strong customer-facing and stakeholder management skills
• Proven ability to prioritize effectively, remove blockers, and drive process improvements
• Bachelor's degree, bootcamp certificate, or equivalent practical experience in Information Technology, Computer Science, or a related field preferred

Preferred Qualifications • Experience using SQL for data review, troubleshooting, or querying
• Familiarity with JavaScript or another programming language
• Familiarity with Agile methodologies
• Experience in a fast-paced technology, SaaS, logistics, or platform support environment
• Experience creating or improving SOPs, troubleshooting documentation, and internal knowledge base content
• Demonstrated ability to identify recurring issues and implement scalable process improvements