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

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.

Requirements

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

Benefits

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