Remote Chat Support Agent Jobs in Wakefield, MA (NOW HIRING)

Location: Remote (US East Coast) Schedule: 3:00 AM - 12:00 PM Eastern Time (supporting EMEA/APAC customers)

Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. 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. 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
  

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.

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 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.

• 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

• 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.

• Total compensation is 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

• Huge impact opportunity: Build and scale a company from the ground up
• Competitive compensation: Includes a combination of cash base and commission compensation
• Work on a daily basis with the founding team and mentors
• Join a fun, inclusive and highly motivated team culture (and help define it!)