Stealth AI Startup: Remote Nuanced AI Data Training

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