Senior Executive and Personal Assistant to Founder (US Hours, Travel) at Scalesource

, , Costa Rica -

Full Time

Start Date

Immediate

Expiry Date

17 May, 26

Salary

1500.0

Posted On

16 Feb, 26

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Executive Scheduling, Calendar Management, Inbox Triage, Communication Gatekeeping, Drafting Communications, Social Media Management, Vendor Management, Asset Management, Travel Planning, Event Support, Tech Stack Management, AI Tools Proficiency, High Discretion, Written English, Proactive Follow-through, Negotiation

Industry

Staffing and Recruiting

Description

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 $1,500 USD Monthly starting salary $12,000 Per Year in Bonus Opportunities Flexible Schedule Paid Travel Tech Stack Allowance Executive Level Training Opportunities

Responsibilities

This high-trust role involves running the executive’s schedule and communication flow, organizing inboxes, managing logistics like travel and events, and coordinating vendors and personal assets for the founder and family. Key duties include managing complex calendars, acting as an inbox gatekeeper, executing a culture calendar, and supporting tech stack and asset management.