Tier 2 Support Specialist - Freelance, Remote

About the Client Our client is an AI-enabled technology support provider built exclusively for the restaurant industry, offering 24/7 coverage across POS, KDS, online ordering, networking, and other core restaurant tech platforms. They serve multi-unit restaurant brands nationwide, combining a "we solve it ourselves" philosophy with fast, always-on responsiveness so restaurant teams can stay focused on running their business instead of fighting their tech. Their support model is built on tiered, structured escalation — ensuring every issue reaches the right level of expertise quickly, without unnecessary back-and-forth for the customer. Why does this role exist? Frontline agents resolve routine, first-contact issues quickly — but restaurant technology problems don't stop there. Point-of-sale failures, networking outages, and platform-specific configuration issues need someone with deeper technical know-how who can pick up where Tier 1 leaves off, diagnose the real root cause, and close the loop without customers having to repeat themselves. This role exists to be that next layer of expertise: someone who can take a well-documented escalation and turn it into a confident resolution, protecting both the customer relationship and the restaurant's ability to keep operating without disruption. The Impact you’ll make Escalation Ownership & Resolution Receive and take ownership of escalated tickets from Tier 1 with full troubleshooting context Diagnose and resolve more complex technical issues beyond first-contact scope Close the loop with customers clearly once a resolution is reached Technical Troubleshooting & Execution Provide hands-on support for POS platforms (e.g., Toast, PAR, NCR Aloha), online ordering, and networking issues Investigate root causes rather than applying temporary workarounds Coordinate with third-party vendors when an issue requires external support Ticket Hygiene & Queue Management Fully review escalated tickets before taking action, validating subject line, problem statement, type, category, platform, and priority Maintain SLA alignment and keep the escalations queue current and organized Ensure any further escalation includes complete documentation and troubleshooting history Customer Communication Communicate clearly, calmly, and professionally, especially when resolution requires more time Provide realistic timelines and avoid over-promising resolution Keep customers informed and confident throughout multi-step troubleshooting Knowledge Base & Process Contribution Use and help maintain internal documentation and predefined workflows Flag outdated, missing, or unclear documentation Share recurring issue trends and root-cause patterns with Shift Leads and the Support Operations Manager Skills, Knowledge and Expertise Required: 1–2+ years of customer support or helpdesk experience Hands-on experience supporting restaurant POS or technology platforms (e.g., Toast, PAR, NCR Aloha) Strong phone presence and verbal communication skills Clear written communication and ticket documentation ability Comfortable working in high-volume, multi-channel support environments Your superpowers are... Technical: Working knowledge of restaurant POS systems and related technology stacks Comfort troubleshooting networking, online ordering, and integration issues Ticketing system fluency (Zendesk experience a plus) Ability to multitask across tickets, chat, and calls without losing accuracy Soft Skills: Calm, clear communicator under pressure Strong problem-solving instincts and root-cause thinking Highly organized with sharp attention to detail Collaborative — knows when to loop in Shift Leads or SMEs WFH Set-Up: Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up. Internet speed of at least 40MBPS Headset with an extended mic that has noise cancellation and a webcam Back-up computer and internet connection Quiet, dedicated workspace at home You should apply if... You genuinely enjoy solving technical problems and don't stop at the first workaround — you want to understand why something broke. You stay composed when a customer is frustrated, because you know clear communication and a realistic timeline matter more than a rushed answer. You take ownership of your queue, document your work thoroughly, and see clean handoffs as a point of pride, not an afterthought. You're energized by fast-paced, high-volume environments and see every escalation as a chance to prove the team's expertise. What to expect... Work Setup: Remote position Must have a reliable internet connection and a quiet workspace Required to provide own computer with Intel Core i5 or something similar or higher operating system Working Hours: 40 hours per week U.S. Business Hours Compensation: $7 per hour No benefits package included Benefits