Executive Assistant to CEO

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 (Philippine-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 professionals

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 hrs/week) - we're flexible for the right person
• Compensation: Competitive salary based on experience (discussed during interview)
• Eligibility for 13th-mo pay after three months of employment
• Eligibility for paid vacation and sick leaves after three months of employment
• WiFi 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.)

We're reviewing applications on a rolling basis and will move quickly for exceptional candidates.
Interview Process:
We respect your time. Our process is:

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

Ready to become the CEO's secret weapon? Apply now