Executive Assistant to the Founder

Executive Assistant To The Founder Location: Remote Employment Type: Full-time IC Hours: Meaningful daily overlap with U.S. Pacific Time (live calendar management and a daily communication rhythm are core to the role) About The Role As the business scales, the Founder can no longer personally hold every owner relationship, inbound lead, and scheduling decision. This role exists to protect the Founder's time and act as a trusted extension of him — owning communications, sales administration, and calendar management so he can focus on high-value sales conversations and growth. This is a high-trust, high-autonomy role spanning communications, sales administration, and calendar management — not a traditional inbox-and-scheduling EA position. The right person will develop real fluency in how the business operates so they can represent it accurately and confidently in communications with property owners and prospective clients. Key Responsibilities Email & Client Communications Manage the Founder's inbox so only items genuinely requiring his attention reach him — decisions only he can make, or relationships he needs to personally maintain. Respond directly to routine correspondence and close it out. Handle escalated property-owner communications on topics such as guest damage claims, utility billing questions, and property performance, working from established documentation and internal guidelines. Notice recurring questions or friction points from clients and flag them as opportunities to improve how we communicate or operate. Draft and send recurring owner updates and communications in the Founder's voice. Sales Administration & CRM Organize and maintain lead records in the CRM, keeping details accurate and current. Handle administrative sales communication — sending contracts or templates, scheduling, and follow-up nudges — while substantive sales conversations remain with the Founder. Maintain clean, reliable sales and marketing data for reporting. Prepare brief context and background ahead of the Founder's sales and discovery calls. Calendar Management Manage the Founder's calendar for sales/discovery calls, networking, and marketing-related meetings. Screen incoming meeting requests, distinguishing genuine opportunities from generic outreach, and book directly within his normal availability. Flag anything ambiguous or unusual rather than making a unilateral call in either direction. Working Style & Communication Operate with an autonomy-first, high-trust approach: act and use good judgment on routine matters rather than waiting for approval. Route the defined set of sensitive matters directly to the Founder — legal matters, financial commitments above a set threshold, safety issues, anything involving a regulator or legal counsel, and anything public-facing. Maintain a daily working rhythm, meet the defined turnaround on anything submitted for review, and provide proactive updates — at least daily — on anything that takes more than a day to resolve. Required Qualifications Strong written communication skills, with the ability to represent a business credibly and professionally to clients. Sound judgment under ambiguity, including a clear sense of what to handle independently versus escalate. Demonstrated ability to take initiative and own outcomes without step-by-step instructions. Comfort working autonomously in a fast-moving, founder-led environment. Reliable daily availability with meaningful overlap with U.S. Pacific Time. Preferred Qualifications Experience supporting a founder, executive, or small business owner across inbox and client communications. Background in property management, real estate, hospitality, or a related client-facing field. Familiarity with the short-term rental (STR) or Airbnb space — a strong plus, as the operational skills transfer directly to our furnished mid-term rental model. Hands-on experience with GoHighLevel or similar. Experience owning client or customer communications on sensitive or escalated topics. Ideal Candidate Profile You are: A strong writer who can adopt the Founder's voice and communicate with property owners with clarity and confidence. Judgment-driven — you know when to act and when to flag, and you're comfortable making the call on routine matters. Genuinely curious about the business — you want to understand our services, clients, and commitments well enough to represent them credibly, not just execute tasks. Proactive and ownership-minded — you close loops, follow up without being asked, and keep the Founder informed. Calm under friction — escalated client issues don't rattle you; you work them through methodically. Reliable and self-directed — you thrive in an autonomy-first culture and don't need heavy structure to perform. Why Join Us You'll work directly with the Founder of a growing, well-regarded company in the furnished-rental space, with real ownership over how we communicate and operate. This is a role with genuine autonomy and room to grow as the business expands into new markets — for someone who wants to be trusted as a true extension of the business, not just an assistant. Somewhere