AI Native Executive Assistant

We're looking for an AI Native Executive Assistant to build and maintain the operational infrastructure of a fast-moving AI health technology company operating across two distinct business verticals. You will own the company's internal operating system, implement and integrate the AI toolstack, automate recurring processes, and serve as chief-of-staff support to the founder. This is not a traditional executive assistant role. You will be expected to build tools and automations independently using no-code and low-code platforms, configure cross-platform workflows, and proactively identify manual processes and replace them with scalable systems. You do not need a traditional engineering background, but you need to be genuinely comfortable building with AI tools and automation platforms. If you are operationally sharp, AI-native, and take pride in creating systems that eliminate repeated work, this role is a strong fit. 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 This role requires availability during US business hours Direct access to the founder of an early-stage AI health technology company building across clinical and performance verticals High-ownership role where your systems and automations directly shape how the company operates What You'll Work On Company Operating System Build and maintain a centralized company operating system in Notion including documentation of goals, OKRs, meeting notes, and project context Eliminate repeated conversations and scattered information by creating a single source of truth across the organization Keep documentation current, organized, and easy to navigate as the company scales AI Toolstack Implementation and Integration Implement and integrate the company's AI-native toolstack including Grain for meeting recording, Attio CRM, Linear for task tracking, and other automation tools Configure permissions, workflows, and integrations to ensure seamless cross-platform operations Stay current on new tools and proactively recommend additions or replacements that improve operational efficiency Process Automation Audit and automate recurring operational processes on a regular cycle, proactively identifying manual tasks and replacing them with scalable systems Use tools such as Claude, Cursor, Zapier, Make, or similar no-code and low-code platforms to build internal automations without requiring deep traditional engineering knowledge Build automations such as auto-populating Linear from monthly goals and other cross-platform workflows that reduce manual effort Chief of Staff Support Track founder follow-ups, manage action items, and ensure nothing falls through the cracks across two distinct business verticals Book travel, coordinate scheduling, and manage logistics on the founder's behalf Maintain visibility across both business lines and surface blockers, priorities, and pending decisions proactively What You Bring Proven experience in an executive assistant, chief of staff, or operations role with a strong systems-building component Demonstrated ability to build workflows and automations using no-code or low-code platforms such as Zapier, Make, n8n, or similar tools Hands-on experience with AI tools such as Claude, ChatGPT, or Cursor in a professional or operational context Experience building and maintaining Notion workspaces including documentation, OKRs, and project management systems Familiarity with tools such as Linear, Attio, or similar task tracking and CRM platforms Highly organized with strong follow-through and the ability to manage multiple priorities across parallel workstreams Proactive and self-directed with a bias toward building systems rather than managing tasks manually Excellent written English communication skills Nice to Have Experience supporting a founder or executive across multiple business verticals simultaneously Background in an early-stage startup or high-growth technology company Familiarity with Grain or similar meeting intelligence and recording platforms Experience with basic scripting or prompt engineering to extend automation capabilities Exposure to health technology, clinical operations, or performance and wellness industries How to Apply Please include: Your updated resume A short Loom video (1 to 2 minutes) introducing yourself, walking through a specific automation or system you built that replaced a manual process, and describing the tools you used and the outcome it produced Only candidates who submit a Loom video will be moved to the next step of the hiring process. If you are genuinely AI-native, take ownership of operational infrastructure, and want to build the systems behind a company doing meaningful work in health technology, this role gives you the access and the latitude to do your best work. 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.