Technical Support Lead

Orlando, FL

Full Time

Mid Level

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

About OneRail

OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

OneRail was named to the Deloitte Technology Fast 500™ two years in a row, was ranked 19th in the 2025 FreightTech 25, named for the fifth year in a row to the FreightTech 100, was honored as one of Inc. magazine’s Best Workplaces 2023, was listed on Forbes’ lists of America’s Best Startup Employers for the last three years, was named to the Inc. 5000 two years in a row and was selected as the Last Mile Company of the Year for the 2024 SupplyTech Breakthrough Awards. To learn more about OneRail, visit OneRail.com.

About OneRail

OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

Apply for this position

Required*

First Name*

Last Name*

Email Address*

Phone*

Address

Resume*

We've received your resume. Click here to update it.

Attach resume or Paste resume

Attach resume as .pdf, .doc, .docx, .odt, .txt, or .rtf (limit 5MB) or Paste resume

Paste your resume here or Attach resume file

Cover Letter

Are you willing to relocate?

What's your citizenship / employment eligibility?

What's your highest level of education completed?

Are you 18 years of age or older?

LinkedIn Profile URL:

Website, blog or portfolio:

Desired salary

In 150 characters or fewer, tell us what makes you unique. Try to be creative and say something that will catch our eye!

150

How many years of experience do you have in technical support, IT support, or a similar customer-facing technical role?*

Please describe your experience serving as a senior technical resource, escalation point, mentor, or informal team lead.*

What experience do you have troubleshooting APIs, integrations, or complex platform issues? Please be specific.*

Which of the following technical skills have you used in a professional setting? Select all that apply.* RestAPIsSQLJavaScriptTroubleshooting Software IntegrationsTechnical documentation/SOP creation

Describe your experience with process optimization, creating SOPs or other technical documentation, and building dashboards.*

Describe a complex technical support issue you owned from initial triage through resolution. What was the issue, how did you investigate it, and what was the outcome?*

Tell us about a time you identified a recurring support problem or process gap and helped improve it. What did you change, and what was the impact?*

While OneRail is open to remote work for some positions, all OneRail team members are required to be willing and able to make occasional visits to our Orlando, Florida headquarters. Are you willing and able to travel to OneRail headquarters for onboarding and on an as-needed basis thereafter?*

At this time OneRail is NOT able to provide sponsorship to candidates for this role who are not currently authorized to work in the US without additional VISA sponsorship. If offered a role with OneRail would your employment require such sponsorship?*

Conflict of Interest Disclosure: To ensure compliance with OneRail’s employment policies, please indicate whether you currently have, or have had, any family members or close relatives employed by OneRail.*

OneRail Employment Status: Have you ever been employed by OneRail?
*This question is used for internal tracking and reporting purposes only. Your response will not affect eligibility or consideration for employment in any way. OneRail is an Equal Opportunity Employer and complies with all applicable employment laws*

Human Check*

Submit Application

Thanks for visiting our Career Page. Please review our open positions and apply to the positions that match your qualifications.

Technical Support Lead

Apply for this position