Executive Assistant to CEO | Outside Hire | Remote (Philippines) | Full-Time or Part-Time (Remote)

CashJar.com; Metro Manila; Remote; PHP 400,000 - 600,000; Full time

Job summary

A dynamic startup is seeking an Executive Assistant to support the CEO in the Philippines. This non-traditional role involves managing the CEO's schedule, communication tasks across two companies, and creating systems for organizational efficiency. The ideal candidate will possess exceptional English skills, a proactive mindset, and tech-savviness, ensuring they effectively support high-impact decisions in a fast-paced environment.

Benefits

Competitive salary based on experience

Flexible remote work hours

Professional development opportunities

Wi-Fi allowance

Equipment stipend

AI tools access

Qualifications

• A minimum of 2 years of relevant experience is preferred.
• Experience in executive support in a tech or dynamic environment is a plus.
• Ability to communicate effectively with various stakeholders.

Responsibilities

• Manage and triage the CEO's email inbox.
• Own the CEO's calendar and manage task prioritization.
• Execute data entry and create dashboards for tracking.
• Anticipate the CEO's needs and propose solutions.
• Handle initial customer support inquiries.

Skills

Exceptional English (written and verbal)

Proactive mindset

Problem-solving skills

Extreme organization

Tech-savvy

Discretion

Tools

Google Workspace

Slack

Jira

Trello

Microsoft Office

Job description

About Outside Hire

Outside Hire is a growing company with over 75 employees, building custom products and solutions for our clients. We’re dynamic, fast‑paced, and always evolving – which means we need someone exceptional to keep our CEO focused on what matters most.

About the Role

We’re seeking an outstanding Executive Assistant to partner with our CEO (Philippines‑based), who runs two companies simultaneously. This isn’t your typical EA role – you’ll be a strategic right hand, problem solver, and force multiplier who helps create more time for high‑impact decisions.

If you thrive on variety, love bringing order to chaos, and want to be essential to a founder’s success, this is your opportunity.

What You’ll Own

Communication & Coordination

• Manage and triage CEO's email inbox (draft responses, handle routine inquiries, flag priorities)
• Collect weekly updates from teams across both companies and our 75+ employees
• Serve as the communication bridge between departments and businesses
• Handle initial customer support inquiries for new product launches

Time & Task Management

• Own the CEO's calendar with strategic time blocking and meeting optimization
• Maintain and prioritize the master task list across both companies
• Proactively identify what can be delegated, automated, or eliminated
• Ensure nothing falls through the cracks

Data & Operations

• Execute data entry and spreadsheet work (you’ll receive direction, you’ll execute with precision)
• Create dashboards and reports to track key metrics
• Document processes and build systems for scale
• Research and analyze information for business decisions

Strategic Support

• Anticipate needs before being asked
• Identify inefficiencies and propose solutions
• Take ownership of projects from start to finish
• Act as an extension of the CEO's thinking and priorities

What Makes You Perfect for This

Must‑Haves

• Exceptional English (written and verbal) – you’ll be drafting emails and communicating on behalf of the CEO
• Proactive mindset – you see what needs to happen and make it happen without waiting to be asked
• Problem‑solving skills – you think critically, creatively, and outside the box
• Extreme organization – you can juggle multiple priorities across two businesses without dropping balls
• Tech‑savvy – Experience with or ability to quickly learn: Google Workspace, Slack, Jira, Trello, and Microsoft tools
• Discretion – you’ll handle confidential information with absolute professionalism

Bonus Points

• Previous EA or executive support experience
• Experience supporting founders or fast‑paced executives
• Background in customer support or operations
• Familiarity with US business hours (some overlap required)
• Experience in tech or agency environments

What You’ll Love About This Role

• ✅ Variety – No two days are the same; you’ll work across strategy, operations, customer experience, and more
• ✅ Impact – Your work directly affects the CEO’s effectiveness and company growth
• ✅ Growth – Learn the inner workings of running two businesses; potential to grow into operations or management roles
• ✅ Autonomy – Once you prove yourself, you’ll have significant independence and decision‑making authority
• ✅ Flexibility – Remote work with flexible hours (though some availability during US business hours needed)

Compensation & Benefits

• Schedule: Full‑time (40 hrs/week) or Part‑time (20‑25 hrs/week) – we’re flexible for the right person
• Compensation: Competitive salary based on experience (discussed during interview)
• Eligibility for 13th‑month pay after three months of employment
• Eligibility for paid vacation and sick leaves after three months of employment
• Wi‑Fi Allowance – We cover your internet costs
• Equipment Stipend – We ensure you have what you need to succeed
• AI Tools Access – Paid subscriptions to AI tools to help you work smarter
• Professional Development – We invest in your growth and learning
• Travel Opportunities – Potential paid travel if business needs arise
• Start Date: Immediately – we’re ready to onboard the right candidate fast
• Location: Remote (Philippines‑based)
• Work Hours: Flexible with some overlap with US time zones (specific hours negotiable)

Tools You’ll Use

Google Workspace, Slack, Jira, Trello, Microsoft Office, and various AI productivity tools.

Our Ideal Candidate is Someone Who

• Thrives in fast‑paced, evolving environments
• Sees problems as opportunities to create better systems
• Communicates clearly and professionally
• Takes pride in making someone else wildly successful
• Thinks outside the box and brings creative solutions
• Wants to be indispensable, not just helpful

How to Apply

Please submit your application with:

• Resume/CV
• Cover letter answering these questions:
  • Describe a time you anticipated someone’s needs before they asked.
  • What’s your approach to managing competing priorities?
  • Why are you interested in supporting someone running two companies?
  • What does "thinking outside the box" mean to you? Give an example.
• Brief writing sample (draft an email responding to this scenario: A customer is asking for an update on their project launch. The project is running 2 days behind due to a technical issue your team is resolving. Write a professional response.)

Interview Process

• Application review (24–48 hours)
• Phone/video screening (20 minutes)
• Working interview with real scenarios (60–90 minutes)
• Reference check + offer

Ready to become the CEO’s secret weapon? Apply now!