[Hiring] Executive Assistant @Penbrothers

Role Description

We are hiring a remote Executive Assistant, based in the Philippines, to support our CEO directly. Our client is a fast-growing B2B software company headquartered in New York, selling to large US property-management firms.

You will be the CEO's right hand:

• Running his calendar, coordinating his meetings with customers, prospects, and investors.
• Taking care of the admin and follow-ups that pull him away from the work only he can do.
• Speaking and writing with senior people in the US every day; confident, fluent spoken English is essential.

This is a full-time, long-term role working US Eastern hours.

What you’ll do

• Calendar and meetings:
  • Own the CEO's calendar end to end: schedule, reschedule and protect focus time, and keep it tidy across US and Irish time zones.
  • Coordinate meetings with customers, prospects, investors, and the team: find times, send invites, book rooms or video links, and chase confirmations.
  • Prepare the CEO for each day: a short daily agenda, who he is meeting, background on each person, and any materials he needs.
  • Take notes in meetings where asked and track follow-up actions until they are closed.
• Prospect and customer gifting:
  • Run our gifting programme for prospects and customers: pick, order, personalise and ship gifts to US addresses, and keep a log of what went to whom and when.
  • Draft the accompanying notes in the CEO's voice.
• Making the CEO's job easier:
  • Manage his inbox: triage, flag what needs a reply, draft responses for him to approve, and make sure nothing important slips.
  • Book travel, accommodation and restaurants, and build clear itineraries.
  • Submit his expenses and keep receipts in order.
  • Handle ad-hoc research, document formatting, data entry, and CRM updates.
  • Keep contact lists, templates, and recurring processes documented and up to date.
  • Spot things that are taking his time and propose a way to take them off his plate.

Qualifications

• Fluent, confident spoken and written English.
• 3+ years as an Executive Assistant, Virtual Assistant or similar, supporting a founder, CEO or senior leader, ideally for US or UK clients.
• Proven experience managing a busy executive calendar across time zones.
• Highly organised and detail-oriented: nothing gets lost, dates and names are always right.
• Proactive: you anticipate what is needed, chase without being asked and suggest better ways of doing things.
• Discreet and trustworthy with confidential information.
• Comfortable with Google Workspace (Gmail, Calendar, Drive), Slack, Zoom and a CRM (HubSpot or similar).
• Able to work US Eastern hours (roughly 9 pm to 6 am Philippine time), from a quiet home office with reliable internet and a backup connection.

Nice to have

• Experience at a startup or small, fast-moving company.
• Experience with corporate gifting or event coordination.
• Familiarity with sales tools (HubSpot, LinkedIn Sales Navigator) and basic CRM hygiene.
• Experience with travel booking for US domestic and transatlantic trips.
• Light project-coordination experience (tracking actions across a team).

Benefits

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.