Stealth AI Startup: Remote Nuanced AI Data Training

<p> <strong>Headquarters:</strong> Seattle, WA <br /><strong>URL:</strong> <a href="https://www.linkedin.com/company/howie-howie/">https://www.linkedin.com/company/howie-howie/</a> </p> <p>We’re building AI systems that help busy professionals manage scheduling, communication, and operational coordination at a very high standard.</p> <p>We’re looking for sharp, fast-thinking operators to help train and improve our AI executive assistant systems.</p> <p>This is not traditional data labeling. The role requires judgment, attention to detail, communication intuition, and the ability to make nuanced decisions quickly in fast-moving situations.</p> <h2>What You’ll Do</h2> <ul> <li>Review and improve AI-generated scheduling and communication workflows</li> <li>Identify unclear, risky, or incomplete AI responses</li> <li>Make judgment calls around calendars, timing conflicts, customer preferences, and tone</li> <li>Ensure messages are specific, actionable, and context-aware</li> <li>Flag edge cases and operational issues that could impact customer experience</li> <li>Help train the AI to behave more like a thoughtful human assistant</li> <li>Work quickly while maintaining strong accuracy and consistency</li> </ul> <h2>Ideal Candidates</h2> <p>You may be a fit if you:</p> <ul> <li>Thrive in fast-paced environments</li> <li>Have strong written communication instincts</li> <li>Naturally catch details others miss</li> <li>Can think critically without relying heavily on rigid rules</li> <li>Are comfortable making decisions with imperfect information</li> <li>Learn systems quickly and adapt to changing workflows</li> <li>Have experience in operations, executive assistance, hospitality, customer support, coordination, recruiting, or similar high-context work</li> </ul> <p>You do <strong>not</strong> need to be an engineer or technical expert.</p> <h2>Requirements</h2> <ul> <li>Excellent English communication skills</li> <li>Strong internet connection</li> <li>MacBook required</li> <li>Ability to work independently and manage time effectively</li> <li>Comfortable receiving direct feedback and iterating quickly</li> <li>Available for consistent weekly hours</li> </ul> <h2>Nice to Have</h2> <ul> <li>Experience supporting executives or clients</li> <li>Familiarity with AI tools such as <a class="decorated-link" href="https://chatgpt.com?utm_source=chatgpt.com">ChatGPT</a> or <a class="decorated-link" href="https://claude.ai?utm_source=chatgpt.com">Claude</a></li> <li>Experience in startups, operations, scheduling, or remote support environments</li> <li>Strong pattern recognition and organizational instincts</li> </ul> <h2>What Success Looks Like</h2> <p>Successful trainers are:</p> <ul> <li>Fast without being careless</li> <li>Calm under pressure</li> <li>Thoughtful communicators</li> <li>Highly reliable</li> <li>Able to balance customer experience with operational efficiency</li> <li>Comfortable owning decisions rather than escalating every edge case</li> </ul> <p><strong>To apply:</strong> <a href="https://weworkremotely.com/remote-jobs/stealth-ai-startup-remote-nuanced-ai-data-training">https://weworkremotely.com/remote-jobs/stealth-ai-startup-remote-nuanced-ai-data-training</a></p>