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.
