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 JoinYou will be paid in USD (bi-monthly: every 15th and 30th)Paid Time Off in accordance with company policyObservance of Holidays per company guidelines100% remote setup so you can work wherever you're most productiveThis role requires availability during US business hoursDirect access to the founder of an early-stage AI health technology company building across clinical and performance verticalsHigh-ownership role where your systems and automations directly shape how the company operatesWhat You'll Work OnCompany Operating SystemBuild and maintain a centralized company operating system in Notion including documentation of goals, OKRs, meeting notes, and project contextEliminate repeated conversations and scattered information by creating a single source of truth across the organizationKeep documentation current, organized, and easy to navigate as the company scalesAI Toolstack Implementation and IntegrationImplement and integrate the company's AI-native toolstack including Grain for meeting recording, Attio CRM, Linear for task tracking, and other automation toolsConfigure permissions, workflows, and integrations to ensure seamless cross-platform operationsStay current on new tools and proactively recommend additions or replacements that improve operational efficiencyProcess AutomationAudit and automate recurring operational processes on a regular cycle, proactively identifying manual tasks and replacing them with scalable systemsUse tools such as Claude, Cursor, Zapier, Make, or similar no-code and low-code platforms to build internal automations without requiring deep traditional engineering knowledgeBuild automations such as auto-populating Linear from monthly goals and other cross-platform workflows that reduce manual effortChief of Staff SupportTrack founder follow-ups, manage action items, and ensure nothing falls through the cracks across two distinct business verticalsBook travel, coordinate scheduling, and manage logistics on the founder's behalfMaintain visibility across both business lines and surface blockers, priorities, and pending decisions proactivelyWhat You BringProven experience in an executive assistant, chief of staff, or operations role with a strong systems-building componentDemonstrated ability to build workflows and automations using no-code or low-code platforms such as Zapier, Make, n8n, or similar toolsHands-on experience with AI tools such as Claude, ChatGPT, or Cursor in a professional or operational contextExperience building and maintaining Notion workspaces including documentation, OKRs, and project management systemsFamiliarity with tools such as Linear, Attio, or similar task tracking and CRM platformsHighly organized with strong follow-through and the ability to manage multiple priorities across parallel workstreamsProactive and self-directed with a bias toward building systems rather than managing tasks manuallyExcellent written English communication skillsNice to HaveExperience supporting a founder or executive across multiple business verticals simultaneouslyBackground in an early-stage startup or high-growth technology companyFamiliarity with Grain or similar meeting intelligence and recording platformsExperience with basic scripting or prompt engineering to extend automation capabilitiesExposure to health technology, clinical operations, or performance and wellness industriesHow to ApplyPlease include:Your updated resumeA 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 producedOnly 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 OverviewOur comprehensive selection process ensures we find the rig