Job Description

 About Penbrothers

Penbrothers is an HR & remote talent management partner and one of the fastest-growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes.

About the Client

Our client processes millions of contract data points across your portfolio, building a real-time intelligence layer that uncovers hidden costs, validates operating spend, and surfaces portfolio risks fragmented systems miss.

About the Role

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, and taking care of the admin and follow-ups that pull him away from the work only he can do. You will speak and write with senior people in the US every day, so 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

What You Bring

• 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)

Our Hiring Process & AI Disclaimer: We use AI tools to streamline our application process—including an initial conversation with an AI Interviewer. All hiring decisions are made entirely by humans: our Talent Acquisition team guides your full candidate journey and makes all evaluation decisions.

You are welcome to use AI for CV refinement and research, but real-time AI assistance during interviews or skill assessments is strictly prohibited to ensure an authentic evaluation.

Read our full AI Disclaimer to learn more

What You’ll Get

At Penbrothers, we are obsessed with creating positive employee experiences. Here you’ll find an environment that nurtures learning and provides opportunities for growth. You’ll have the opportunity to make an impact on fast-growing startups and dynamic companies.

· 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.