[Hiring] Senior Technical Support Agent @Yoodli AI Roleplays

Role Description

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.

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.
• 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!

Responsibilities

• 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.
• 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.
• Determine and implement effective solutions to complex issues.
• Create and communicate clear, thoughtful action plans to customers, including enterprise stakeholders.
• Partner closely with Engineering, Product, and other internal teams to escalate, track, and resolve complex or systemic issues.
• Identify patterns across tickets and proactively flag recurring or emerging issues.
• Contribute to and help maintain support documentation, internal playbooks, and troubleshooting guides.
• Mentor and coach newer support agents on troubleshooting technique, tone, and prioritization.
• Stay current on Yoodli's fast-moving AI platform.
• Manage time effectively across competing priorities, a fast-paced ticket queue, and mentorship responsibilities.

Qualifications

• 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.
• 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.
• 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.

Bonus

• Advanced proficiency in HubSpot or a similar CRM/ticketing platform.
• 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.
• Experience working with Learning Management Systems (LMS), including SCORM and LTI integrations.

Benefits

• Total compensation targeted at $89,600 - $103,000 (depending on experience).
• Equity opportunities at a fast-growing company.
• Health, dental, vision insurance.
• 401k plans.
• Unlimited PTO, free lunches at the office.