Remote Nuanced AI Data Training
Role Overview
This role involves reviewing and improving AI-generated scheduling and communication workflows, making nuanced decisions around calendars, timing, tone, and customer preferences. It's a mid-level position on a fast-moving AI training team, requiring sharp judgment and attention to detail to help refine an AI executive assistant system. The impact includes directly shaping AI behavior to be more thoughtful and context-aware.
Perks & Benefits
Fully remote position with worldwide availability, offering flexible hours and consistent weekly work. You'll work with a cutting-edge AI startup, gaining experience in AI training and operations. The role emphasizes autonomy and fast iteration, with direct feedback loops. Career growth potential in AI and operations.
Full Job Description
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
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