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 (20-25 hrs/week) - we're flexible for the right person
- Compensation: Competitive salary based on experience (discussed during interview)
- Eligibility for 13th-mo pay after 1 year 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
- A 1-2 minute self-introduction video that includes a summary of your experience as an EA and what makes you the best match for this role
- 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 (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!