About the role
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