Support live deployments of AI systems for an early-stage AI company
Review live AI-driven interactions including call transcripts and text messages to ensure accuracy and quality
Identify inconsistencies, edge cases, and failure patterns across high volumes of outputs
Flag issues proactively including when expected system updates are missing or delayed
Interpret ambiguous or incomplete situations and determine the appropriate next step independently
Recognize when an AI interaction has become stale or invalid and take ownership of resolving it
Translate observed issues into clear, structured, and actionable communication for internal teams and customers
Help ensure smooth execution of active pilots and deployments
Maintain organized documentation of edge cases and resolutions
Support the development of processes for handling new scenarios as the product evolves

Background in chief of staff, senior executive assistant, operations lead, or a comparable high-ownership generalist role
Exceptional attention to detail and the ability to spot inconsistencies under high volume
Strong judgment in ambiguous situations: you own the problem, figure it out, and flag it with context
Clear and professional written and spoken English communication
Comfortable navigating multiple platforms such as Slack, Teams, and SMS simultaneously
Highly reliable, responsive, and able to operate in real-time workflows
Available to work 9 AM to 5 PM Eastern Time Monday through Friday

Executive Assistant – AI Operations

Key skills