Work Arrangement: 100% Remote – Philippines
Employment Type: Full-Time | Independent Contractor
Schedule: US Hours / Night Shift or Split Schedule
Salary: ₱55,000 per month
Quarterly Bonus: Up to ₱50,000, tied to performance/Rocks
Start Date: ASAP
JOB OVERVIEW
We are looking for a highly organized, proactive, and strategic Remote Executive Assistant / Chief of Staff (Operator Track) to support the Founder of a multi-entity business and nonprofit ecosystem.
This is not a traditional administrative assistant role. We are looking for someone who can take ownership, anticipate needs, manage priorities, protect the Founder's time, and keep multiple projects and relationships moving without needing to be constantly directed.
You will serve as the operating system between the Founder and the outside world—managing communications, projects, scheduling, relationships, documentation, and follow-through.
The ideal candidate is someone who can think independently, make sound recommendations, communicate with confidence, and take territory rather than simply take orders.
KEY RESPONSIBILITIES
1. Inbox & Communication Management
- Own and manage multiple email accounts, messaging platforms, WhatsApp, and social accounts.
- Build and maintain an effective inbox triage system.
- Identify messages requiring the Founder's direct attention and provide context and recommended actions.
- Draft and eventually send responses on behalf of the Founder within established guidelines.
- Handle routine scheduling, introductions, confirmations, logistics, follow-ups, and declines.
- Maintain inbox zero for routine communications.
- Prepare a daily executive brief covering priorities, items handled, risks, and decisions requiring the Founder's attention.
2. Project & Operations Management
- Maintain a consolidated view of active projects across multiple organizations and entities.
- Track project owners, next actions, deadlines, and deliverables.
- Proactively follow up with stakeholders to ensure commitments are completed.
- Coordinate weekly Level 10 (L10) meetings, including agendas, scorecards, issues, and action items.
- Prepare board, partnership, and executive materials such as presentations, one-pagers, agendas, and briefing documents.
- Identify potential scheduling or project conflicts before they become urgent issues.
3. Calendar Management
- Own the Founder's calendar and scheduling process from end to end.
- Protect deep-work time and other priority blocks.
- Coordinate meetings while considering buffers, travel time, and hard stops.
- Provide meeting briefs before important calls, including relevant background, objectives, and desired outcomes.
4. Relationship & CRM Management
- Maintain accurate CRM records for key contacts and relationships.
- Track how relationships were established, areas of interest, commitments, and previous interactions.
- Manage introductions and ensure promised connections are completed.
- Track commitments made by the Founder and ensure they are followed through.
- Maintain proactive relationship touchpoints with important contacts.
5. Systems, SOPs & Process Improvement
- Document recurring processes and turn them into clear SOPs/playbooks.
- Maintain organized systems and ensure there is a clear source of truth for tasks and information.
- Identify opportunities to improve systems, workflows, and tools.
- Continuously identify administrative work that can be delegated, automated, or removed from the Founder's workload.
REQUIREMENTS
Required:
- 3+ years of experience supporting a Founder, Executive, Investor, or senior leader in a high-volume and relationship-driven environment.
- Excellent written and verbal English communication skills.
- Ability to write polished, natural, and culturally appropriate emails for a US-based audience.
- Exceptional organizational and follow-through skills.
- Highly proactive and able to anticipate needs without waiting for instructions.
- Strong judgment and decision-making skills.
- Comfortable managing multiple priorities and working in a fast-paced environment.
- Comfortable protecting an executive's time and professionally saying no when necessary.
- Highly discreet and trustworthy when handling confidential business, financial, board, and partnership information.
- Able to work independently in a remote/async environment.
- Strong proficiency with digital productivity and communication tools.
Strongly Preferred:
- Experience supporting executives across multiple businesses, organizations, or entities.
- Familiarity with EOS / Traction, including Rocks, Scorecards, Level 10 Meetings, Issues, and To-Do discipline.
- Familiarity with the Buy Back Your Time framework.
- Experience working with US-based nonprofit, civic, community, or business organizations.
- Experience using AI tools for drafting, summarization, research, and workflow optimization.
- Experience with CRM and project management platforms.
TOOLS & TECHNOLOGY
Experience with the following is an advantage:
- Google Workspace
- Basecamp
- Notion
- GoHighLevel / CRM platforms
- Slack
- Zoom
- LinkedIn
- AI productivity tools
You should also be comfortable learning new systems quickly and recommending improvements when existing tools or processes are not working effectively.
WORKING HOURS
Because this is a high-trust, gatekeeper role, real-time responsiveness during the Founder's working hours is important.
For candidates based in the Philippines, available working arrangements may include:
- Night shift to provide direct overlap with US working hours; or
- Split schedule combining overnight inbox/project management with a live overlap window during the evening.
Candidates based in the Philippines should indicate their preferred working-hours model and explain why they believe it is sustainable for them.
FIRST 90 DAYS
Days 1–30 – Absorb
- Learn the Founder's communication style and workflows.
- Shadow the inbox and calendar.
- Build the contact map and inbox triage system.
- Begin developing the communication voice guide.
- Document existing processes and identify areas for improvement.
Days 31–60 – Take the Wheel
- Take ownership of the inbox and calendar.
- Launch the daily executive brief.
- Establish a consolidated project tracking system.
- Support and operationalize weekly L10 meetings.
- Create the first set of SOPs/playbooks.
Days 61–90 – Extend
- Begin sending approved communications on behalf of the Founder.
- Operate the CRM and relationship-management cadence.
- Expand the communication voice guide and templates.
- Take ownership of initial quarterly Rocks.
- Identify the next set of responsibilities that can be removed from the Founder's plate.
PERFORMANCE EXPECTATIONS
Success in this role will be measured through clear operational outcomes, including:
- Daily executive brief delivered consistently.
- Critical messages surfaced promptly with recommendations.
- Routine inbox items cleared daily.
- Active projects maintained with clear next actions and deadlines.
- At least 95% of meetings scheduled without Founder involvement.
- At least 90% of assigned To-Dos closed within 7 days.
- Post-meeting follow-ups completed within 24 hours.
- Promised introductions completed within 5 days.
- At least one new SOP/playbook documented per week.
- Continuous improvement in communication quality and autonomy.
WHO WILL THRIVE IN THIS ROLE
You may be a strong fit if you:
- Think several steps ahead.
- Naturally organize chaos.
- Follow through on commitments—even those made by other people.
- Can make decisions without needing constant approval.
- Are comfortable telling an executive, I don't recommend that, and here's why.
- Can bring solutions rather than simply report problems.
- Stay calm and effective when priorities change quickly.
- Take ownership of outcomes rather than just completing assigned tasks.
- Want to grow into a trusted operational partner to a Founder.
THIS ROLE MAY NOT BE FOR YOU IF:
- You need a task list handed to you every morning.
- You frequently wait for instructions before taking action.
- You become unresponsive when things get busy.
- You prefer purely administrative work.
- You are uncomfortable making recommendations or challenging assumptions.
- You want to execute tasks without understanding the bigger picture.
APPLICATION PROCESS
Interested candidates are encouraged to submit:
- Updated Resume
- A short written response (under 300 words) describing a time when you protected an executive's time from something they wanted to say yes to, including the outcome.
- For applicants based in the Philippines: Indicate your preferred working-hours model (night shift or split schedule) and explain why it is sustainable for you.
- Qualified candidates may be asked to complete a short practical assessment involving inbox prioritization, communication drafting, and decision-making.
Note: Finalists may be invited to participate in a paid two-week trial involving actual work before a final offer is made.
Apply now and take your next step toward becoming a true strategic partner to a Foun
der—not just an assistant.
