Y Combinator Tier 2 Support Specialist - Freelance, Remote
Posted Updated
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.
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
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