Executive Assistant (AI Operations) at Hire Overseas

, , Philippines -

Full Time

Start Date

Immediate

Expiry Date

13 Aug, 26

Salary

0.0

Posted On

15 May, 26

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Quality Assurance, Operational Judgment, Executive Support, Stakeholder Communication, AI Output Review, Problem Solving, Attention To Detail, Process Development, Documentation, Project Coordination

Industry

Staffing and Recruiting

Description

We're looking for an Executive Assistant with a chief of staff or senior operations background to support live deployments of AI systems for an early-stage AI company building coordination tools for home care agencies. This is a high-judgment, high-ownership role that sits at the intersection of quality assurance, operations, and product feedback. You do not need a technical background. You need exceptional attention to detail, the ability to make sound decisions quickly in ambiguous situations, and the communication skills to translate what you observe into clear, structured escalations. If you have spent time as a chief of staff, senior EA, or operations lead where you were trusted to own problems end to end and surface insights without being asked, this role will feel familiar. Why You'll Want to Join You will be paid in USD (bi-monthly: every 15th and 30th) Paid Time Off in accordance with company policy Observance of Holidays per company guidelines 100% remote setup so you can work wherever you're most productive Work directly inside an early-stage AI company where your judgment shapes how the product improves High-visibility role with direct impact on the quality of AI systems that support real home care workers What You'll Work On AI Output Review and Quality Assurance 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 Judgment and Decision Making 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 Apply sound operational judgment in fast-moving, real-time workflows without needing step-by-step direction Escalation and Communication Translate observed issues into clear, structured, and actionable communication for internal teams and customers Communicate across Slack, Teams, and other platforms with professionalism and precision Surface recurring patterns and insights that inform product and workflow improvements Operational Support 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 What You Bring 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 Nice to Have Familiarity with EMR or EHR systems, training available for the right candidate Experience in healthcare, home care, or a similarly regulated environment Spanish or Mandarin language proficiency Prior exposure to AI tools or AI-powered workflows How to Apply Please include: Your updated resume A short Loom video (1 to 2 minutes) introducing yourself, describing a situation where you identified and resolved an ambiguous or unexpected problem independently, and explaining how you communicated it to leadership or stakeholders Only candidates who submit a Loom video will be moved to the next step of the hiring process. If you are a sharp, senior operator who catches things others miss, communicates without being asked, and wants to apply that same instinct inside AI systems that support real home care workers, this role gives you the judgment-driven ownership you thrive on. Application Process Overview Our comprehensive selection process ensures we find the right fit for both you and our clients: Initial Application - Submit your application and complete our prequalifying questions Video Introduction - Record an video introduction to showcase your communication skills and work experience Role-Specific Assessment - Complete a homework assignment tailored to the position (if applicable) Recruitment Interview - Initial screening with our talent team Executive Interview - Meet with senior leadership to discuss role alignment Client Interview - Final interview with the client team you'd be supporting Background & Reference Check - Professional reference verification Job Offer - Successful candidates receive a formal offer to join the team Each stage is designed to evaluate your fit for the role while giving you insights into our company culture and expectations. We'll keep you informed throughout the process and provide feedback at each step.

Responsibilities

The role involves reviewing AI-driven interactions to ensure quality and identifying failure patterns to inform product improvements. The candidate will also manage operational support for active pilots and translate observed issues into actionable internal communications.