Yoodli AI Roleplays - Senior Technical Support Agent - East Coast, Night Shift

• 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, 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. • Important: • 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! • THE TEAM • THE TEAM • The Yoodli Support team consists of support professionals with a strong desire to learn and help customers. They are also the epitome of our core values: Humility, Bias for Action, and Winning Together. As a senior member of this team, you'll be looked to as a model of those values and a resource other agents lean on. • Humility, Bias for Action, and Winning Together. • 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 • BONUS • BONUS • 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.