Yoodli AI Roleplays

Yoodli AI Roleplays

Senior Technical Support Agent - East Coast, Night Shift

United States - East Coast (Remote) · Senior

Sponsorship not specified$90k-$103kDetected 13 days ago
SnowflakeDatabricksRESTHubSpotCRMCustomer SupportCommunicationMentoring

About the role

  • Think of it as the batting cage before the big game, but for communication.
  • Whether it's a sales pitch, manager feedback session, or media interview, Yoodli provides private, judgment-free, just-in-time coaching.
  • Leaders at companies like Google, Databricks, Snowflake, RingCentral, Toastmasters, and Dale Carnegie use Yoodli to ramp reps faster, improve message delivery, and reduce coaching burden on frontline managers.

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, working 3:00 AM - 12:00 PM ET
  • 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
  • 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
  • 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
  • Manage time effectively across competing priorities, a fast-paced ticket queue, and mentorship responsibilities
  • 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.
  • 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

Requirements

  • 4-5 years of experience in a technical customer support/service role, including direct experience with complex, high-stakes, or enterprise-tier accounts
  • 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
  • Comfortable operating with a high degree of autonomy in a fast-paced, hyper-growth startup environment
  • 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
  • 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!

Compensation

  • Total compensation is targeted at $89,600 - $103,000 (depending on experience)
  • Competitive compensation: Includes a combination of cash base and commission compensation

Benefits

  • Equity opportunities at a fast growing company
  • Health, dental, vision insurance
  • Unlimited PTO, free lunches at the office

Company info

  • Yoodli is the AI roleplay simulator redefining how individuals and teams master communication.
  • The result is stronger performance, greater team readiness, and a more scalable path to impact.
  • We're building a new category called Experiential Learning: an AI-powered category that helps people learn through conversational roleplays.
  • People don't learn from slides, they learn through dialogue, questions, and iteration.
  • Yoodli makes that process interactive, personalized, and always up to date.
  • It's learning that feels fun, builds confidence, and finally lets organizations measure the ROI of training.
  • We've raised $40M in Series B funding, are doubling our team in 2026, and are headquartered at the beautiful Pier 70 in Seattle.
  • TED Talk with our "Why"
  • Explainer on experiential learning
  • 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.
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