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