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Senior Executive and Personal Assistant to Founder (US Hours, Travel) at Scalesource. JOB TITLE. Executive & Personal Assistant to Founder (Remote, US Hours) — $1,500 USD/month + Up to $12k/yr Bonus + Paid Travel. LOCATION. Remote. Preferred hiring markets: Colombia, Philippines, South Africa, Kenya, Chile (strong candidates from similar countries may be considered).. COMPENSATION. - $1,500 USD per month base . - Up to $12,000 USD per year in performance bonuses. - All required travel costs covered (flights, lodging, etc.). - Quarterly in-person travel (1x/quarter for 1–2 weeks) required. ROLE TYPE. Full-time, long-term. . ABOUT THE ROLE. This is a high-trust, high-ownership Executive & Personal Assistant role supporting a founder and family. You will run the executive’s schedule and communication flow, keep inboxes organized, manage logistics (travel/events), coordinate vendors and personal assets/properties, and help the team stay organized with the tech stack.. This is not a task-by-task VA role. We need someone “all in” with executive-level judgment, strong written English, and proactive follow-through.. WHAT YOU’LL OWN (RESPONSIBILITIES). Executive schedule & coordination. - Manage personal and business calendar with strong prioritization and protection of focus time. - Coordinate meetings across time zones, confirm details, prep agendas/briefs, and ensure follow-ups happen. Inbox + communications gatekeeping. - Review incoming emails daily and keep inboxes organized (labels, rules, triage). - Draft replies in the executive’s voice, escalate urgent items, and close loops. - Handle inbound calls and messaging (screen, route, respond, and document next steps). Social media support. - Manage personal social media profiles and inbound messages (DMs/comments). - Track conversations and ensure follow-ups are not missed. Culture calendar execution. - Execute the “culture calendar” for the family and team members (birthdays, anniversaries, holidays, gifts, key moments). - Keep reminders and planning organized so nothing is last-minute. Tech stack support. - Help manage the team’s tech stack (accounts, permissions, subscriptions, renewals). - Basic troubleshooting and coordination with vendors/support. - Use AI tools to accelerate drafting, summarizing, research, and SOP creation. Asset + property management. - Manage personal vehicles and properties: utilities, vendor sourcing/management, scheduling maintenance. - Track insurance policies, renewals, and key documents. - Own vendor relationships and negotiate pricing/terms where possible. Travel & events. - Plan and book travel, build clean itineraries, handle changes quickly. - Support events and in-person meetings as needed. Family support. - Support Spouse with various tasks as needed (coordination, research, scheduling, vendor calls, follow-ups). WORKING STYLE + AVAILABILITY EXPECTATIONS. - You will work mostly on US standard time (with meaningful daily overlap).. - You have flexibility during weekdays (gym/errands/etc are fine without asking).. - You must be highly responsive and reliable:. - During agreed working windows: prompt responses and same-day execution.. - Outside standard hours: availability for evenings/weekends as needed.. - You control your schedule as long as meetings are attended and responsiveness remains high.. TRAVEL REQUIREMENT (NON-NEGOTIABLE). - Must be able to travel to the US or other locations at least 1x per quarter for 1–2 weeks.. - Must have a valid passport and be willing/able to obtain appropriate travel authorization (tourist/business visa/ESTA, etc.) as needed.. HOW TO APPLY. Submit your resume + complete the qualifying questions below. If you meet all knock out requirements, you will be REQUIRED to submit a self-recorded introduction video as a next step prior to the interview process. ONLY candidates who meet all knockout requirements and submit an introductory will be prioritized for interviews.. REQUIRED QUALIFICATIONS. - 5+ years of experience as an Executive Assistant / Senior EA / assistant to C-level leaders (CEO/Founder/COO/CRO, etc.). - Strong written and spoken English (professional, concise, high accuracy). - Proven experience managing:. - Complex calendars. - Inbox triage and drafting executive communications. - Travel planning and itineraries. - Vendor management and negotiation experience (you have personally negotiated pricing/terms). - Strong tech competence across common tools:. - Google Workspace and/or Microsoft 365. - Slack/Zoom/Teams. - Project/task tools (Asana, ClickUp, Notion, Airtable, etc.). - Comfort using AI tools for productivity (research, drafting, summaries, SOPs). - High discretion: comfortable handling sensitive personal and business information. - Reliable internet, professional working setup, and strong follow-through. PREFERRED (NICE TO HAVE). - Master’s degree (helpful, but not required if experience is strong). - EOS familiarity (Level 10 meetings, Rocks, Scorecards, IDS). - Experience supporting founders/high-growth companies or family-office style operations. Company Location: Costa Rica.