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# Senior Technical Support Agent - East Coast, Night Shift

- **Company:** Yoodli AI Roleplays
- **Location:** Philadelphia, PA, United States
- **Experience:** Expert
- **Salary:** $89,600.0 - $103,000.0
- **Contract:** Permanent contract
- **Skills:** Application Programming Interfaces (APIs), Artificial Intelligence, Learning Management Systems, Sharable Content Object Reference Model, Systems Integration, Web Applications, Hubspot
- **Published:** July 10, 2026
- **Apply:** https://www.phillyjobs.com/job.asp?id=3316231366&tx=YT1313TTI&pt=1&aff=0B19D771-A501-4A5E-8338-2A822B784D54&utm_source=Job%20Feed&utm_medium=textkernel&utm_campaign=DE&utm_term=0B19D771-A501-4A5E-8338-2A822B784D54

## About the Role

We are seeking a seasoned technical support professional who has already mastered the fundamentals of complex troubleshooting and is ready to raise the bar for the entire team. This is an individual-contributor role with real influence: you'll own the hardest, highest-stakes customer issues, mentor newer agents, and help shape the processes and tooling that let a small team punch above its weight., * 4-5 years of experience in a technical customer support/service role, including direct experience with complex, high-stakes, or enterprise-tier accounts

 * Excellent instincts and judgment for prioritizing high-impact customer issues, deciding when to escalate, and knowing when to push back on an escalation
 * Advanced analytical and critical-thinking skills, with a demonstrated track record of independently diagnosing and resolving hard technical problems
 * Excellent verbal and written communication skills, with the ability to explain technical and AI-specific concepts clearly to both non-technical users and technical stakeholders
 * Demonstrated experience mentoring, coaching, or informally leading other support agents
 * Comfortable operating with a high degree of autonomy in a fast-paced, hyper-growth startup environment
 * A genuine team player who raises the bar for others and has a strong desire to keep learning
 * Deep curiosity and comfort with AI-powered products, including the ability to reason about and explain AI/model behavior to non-technical users, * Advanced proficiency in HubSpot or a similar CRM/ticketing platform, including building or improving processes, workflows, SLAs, or reporting
 * Experience troubleshooting web-based applications, API/SSO integrations, common error messages, and operating system settings at a senior level
 * Experience troubleshooting live with customers via screen share, including in high-pressure or executive-visible situations
 * Experience working with Learning Management Systems (LMS), including SCORM and LTI integrations.

## Description

This role is ideal for someone who has "seen it all" in a technical support seat and wants to bring that experience and judgment to bear on ambiguous, high-visibility problems, while also being a go-to resource for the rest of the team. On a day-to-day basis, you'll troubleshoot the most technical issues for our clients via email and screen share, triage and often personally handle escalations from enterprise accounts, and serve as a technical mentor.

Important: this role supports our EMEA/APAC customer base and requires working 3:00 AM - 12:00 PM Eastern Time.

If you're passionate about AI technology, providing a world-class customer experience, and thrive in a fast-paced, hyper-growth startup environment, this is the career path for you!, * Own and resolve the most technically complex, high-priority, and enterprise-critical tickets via email and live screen share for our growing EMEA/APAC customer base, working 3:00 AM - 12:00 PM ET

 * Independently investigate and diagnose ambiguous or previously unseen technical issues, applying strong root-cause analysis rather than surface-level fixes
 * Serve as a point of technical escalation for the rest of the support team, including reviewing tricky tickets and helping less experienced agents land on the right resolution path
 * Determine and implement effective solutions to complex issues, and know when a problem needs to be escalated to Engineering versus being resolved directly
 * Create and communicate clear, thoughtful action plans to customers, including enterprise stakeholders, in an approachable, confident manner
 * Partner closely with Engineering, Product, and other internal teams to escalate, track, and resolve complex or systemic issues, building strong cross-functional relationships and pushing for durable fixes
 * Identify patterns across tickets and proactively flag recurring or emerging issues before they become widespread
 * Contribute to and help maintain support documentation, internal playbooks, and troubleshooting guides so institutional knowledge doesn't live in one person's head
 * Mentor and coach newer support agents on troubleshooting technique, tone, and prioritization
 * Stay current on Yoodli's fast-moving AI platform, proactively seeking out and sharing new product knowledge with the team
 * Manage time effectively across competing priorities, a fast-paced ticket queue, and mentorship responsibilities


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