Calltree

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: We're a fast-growing startup backed by leading investors in Silicon Valley serving multiple enterprise customers, including public retail brands you'd recognize. We're building AI that actually works for complex, real-world customer service—the kind of calls everyone else avoids. The Role: You'll work alongside AI to serve real customers—and learn how AI actually works in the real world. You'll handle live customer calls—troubleshooting, problem-solving, helping real people. You'll also have AI tools working alongside you, so you can handle more and do more than a traditional rep ever could. You will be working closely with our engineering team to help improve the AI and business processes. What You'll Do: Handle inbound customer calls and chats—real troubleshooting, real problem-solving Use AI tools to actually solve problems De-escalate frustrated customers and turn bad experiences into good ones Follow documented processes to resolve issues correctly Identify patterns and flag insights to help improve how we work (both AI and tooling) What We're Looking For: 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 attention to detail Can stay focused and motivated even when things get repetitive Ability to work one weekend day Flexible schedule (e.g., 10am-7pm or 11am-8pm) Honest Expectations: You'll be on the phone with customers. Some will be frustrated. Some days will be nonstop. But you're not just another call center rep—you're working with AI tools that multiply your impact, helping build something new, and gaining experience that will set you apart. If you want to be part of the future of customer service, not stuck in the past, this is the role. 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 along with a link (unlisted youtube video/google drive link) to 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.