About Calltree: We're a YC W25 company with multiple enterprise customers, including public retail brands you'd recognize. We're building AI that actually works for complex, real-world use cases. For example, our AI handles 30+ minute technical troubleshooting calls—the kind everyone else avoids.
The Role: You'll be the human supervisor behind our AI agents, working with live customer interactions in real-time. You'll monitor how AI performs, ensure quality, and when needed, jump in to rescue conversations and ensure great customer outcomes. You'll also work directly with engineering to make the AI smarter every day.
What You'll Do:
Monitor live AI-customer conversations and ensure quality standards
Make real-time judgment calls on when to intervene
Step in as the escalation point when customers need a human, de-escalating frustrated customers and resolving complex issues
Identify patterns in AI performance and document what's working and what's not
QA new AI experiences before release—interact with them as customers would and flag issues
Work with engineering to improve the AI based on what you observe
Build the playbooks and processes for this function as we scale
What Success Looks Like:
Measurable improvement in AI performance metrics AND customer satisfaction
Good judgment on when to intervene vs. let the AI continue
Catching issues before they hit production
Building institutional knowledge about what makes conversations succeed or fail
What We're Looking For:
Recent college graduate (any field)
Comfortable being on the phone with customers, including frustrated ones
Someone who's excited about AI technology AND genuinely enjoys helping people
Strong judgment and decision-making skills
Ability to work one weekend day
Honest Expectations: This role is a balance of two things: operational monitoring work (watching, reading, documenting) and live customer interaction. Some days will feel repetitive. But you're also accountable for real customer outcomes—when you jump in, you're the person who saves the experience. If you love technology but never want to talk to customers, this isn't the role. If you want both—mastering AI systems AND helping real people—you'll thrive here.
Career Growth: This isn't just a job—it's a launchpad. Top performers have clear paths to become AI Team Leads, move into Product roles, or specialize in AI training and development. You'll gain hands-on experience with cutting-edge AI technology that will set you apart in your career.
To Apply: Send your resume with a short video (2-3 minutes). For the video: pick an appliance or product you have in your house, then roleplay a customer service scenario where you're helping a frustrated customer troubleshoot a problem with it.
About Calltree
Calltree makes enterprise-grade AI support reps for call centers. Our AI reps take voice calls and chats like other AI support agents but can also use internal enterprise tools like a homegrown CRM or internal dashboards, like the highly trained humans working there today.
