Work All Remote

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

Go to posting –> https://weworkremotely.com/remote-jobs/stealth-ai-startup-remote-nuanced-ai-data-training