Executive Assistant (Job ID: MONSAM1EA)

Inside Out Hiring; United States; Remote; USD 25,000 - 33,000; Full time

Job summary

Inside Out Hiring is seeking a remote Executive Assistant or Chief of Staff to support the founder of a premier property management firm focused on affordable housing. The role emphasizes strategic operations, high-volume correspondence, and cross-functional coordination.

The ideal candidate is proactive, highly organized, and fluent in English, with strong MS Office skills, an AI-ready mindset, and excellent communication. Remote work spans international locations, aligning with Pacific Time.

Qualifications

• Fluent English communication, both written and verbal.
• Strong MS Excel and PowerPoint proficiency for org charts.
• Willingness to adopt AI tools to improve productivity and SOPs.
• High emotional intelligence with excellent interpersonal and conflict-resolution skills.

Responsibilities

• Digital Document & Financial Management across multiple property accounts.
• Email triage and drafting responses for ownership groups and partners.
• Represent the executive on calls and meetings during on-site property visits.
• Provide resident and customer service support with patience and efficiency.
• Manage scheduling to protect leadership’s time for strategic priorities.
• Coordinate with ownership groups and internal teams to ensure smooth operations.
• Assist in implementing AI-driven workflows and SOP improvements.

Skills

Flawless English

Emotional Intelligence

AI readiness

Tools

Microsoft Office

Excel

PowerPoint

Outlook

Claude

Yardi

Zoom

Teams

Job description

Exciting Remote Opportunity! We're Hiring an Executive Assistant / Chief of Staff!

Are you a highly proactive, high-EQ professional ready to step into a strategic operational role? We are looking for an exceptional Executive Assistant / Chief of Staff to provide high-level support to the founder of a premier property management firm specializing in affordable housing!

C1 ENGLISH LEVEL IS REQUIRED. The selected candidate will be speaking strictly in English during their whole shift.

Job Details at a Glance

• Job Title: Executive Assistant / Chief of Staff

• Job ID: MONSAM1EA

• Industry: Property Management (Affordable Housing)

• Location: Philippines, LATAM, or South Africa

• Job Status: Full Time

• Work Schedule: Monday to Friday, 8:00 AM to 5:00 PM / 7:00 AM to 4:00 PM Pacific Time

• Salary: $2200 to $3000 per month

• Target Start Date: ASAP

About the Client

The company is a property management firm specializing in affordable housing, overseeing thousands of residential units across approximately fifty properties. The organization works closely with a network of ownership groups and has built its reputation on a hands-on, relationship-driven approach, with leadership regularly visiting properties in person to maintain strong ties with owners and residents. The business maintains an established offshore team supporting accounting and other back-office functions.

The role exists because a senior member of the executive support team is on extended leave, creating a gap in coverage for high-volume administrative operations and strategic support functions. Leadership's time is currently consumed by lower-level operational tasks, including processing physical mail across numerous bank accounts and triaging correspondence from ownership groups, which limits the time available for property visits and business growth activities.

About the Role

You will serve as a remote Executive Assistant or Chief of Staff, providing high-level operational and administrative support to the founder. Your core purpose is to manage a high volume of correspondence, including physical mail processing across multiple bank accounts per property and triaging emails from ownership groups by understanding the relative priority and relationship dynamics of each contact.

You will also represent the executive in calls and meetings while they are engaged in on-site property visits, ensuring continuity of communication and follow-through on commitments. Beyond administrative coordination, you will take on strategic responsibilities that support broader business operations, contributing to decision-making support and cross-functional coordination rather than routine note-taking or minute-keeping.

Key Responsibilities

• Digital Document & Financial Management: Process, categorize, and organize high volumes of digital bank statements, financial correspondence, and documentation via email across multiple property accounts.

• Email Triage & Communication: Monitor executive inboxes, prioritize messages from ownership groups and key partners based on urgency, and draft accurate responses.

• Meeting Representation: Attend and represent the executive on calls and meetings during on-site property visits, ensuring key details are tracked and communicated back to the team.

• Resident & Customer Service Support: Handle incoming phone inquiries with patience and strong conflict-resolution skills—ensuring residents (particularly in affordable housing communities) feel heard and respected while efficiently managing call times.

• Calendar & Communication Coordination: Manage scheduling and calendar management to ensure leadership’s time is protected for property-facing work and strategic priorities.

• Stakeholder & Operations Coordination: Serve as a reliable point of contact for ownership groups and internal teams; support general office administrative needs to keep day-to-day operations running smoothly.

• Process & Workflow Optimization: Work alongside leadership to introduce AI-driven tools and modern workflows to streamline operations, administrative tasks, and SOP creation.

Qualifications & Skills

Non-Negotiable Requirements:

• Microsoft Office Suite: Strong hands-on proficiency in Microsoft Excel and Microsoft PowerPoint (specifically for maintaining organizational charts).

• AI Readiness & Adaptability: Willingness and capability to utilize AI tools to improve daily productivity, document SOPs, and streamline workflow efficiencies.

• Flawless English Communication: Exceptional written and verbal communication skills, capable of handling nuanced, high-stakes correspondence with property owners, internal teams, and external stakeholders.

• High Emotional Intelligence & Empathy: Strong phone presence and active listening skills. Ability to handle sensitive or upset callers (particularly residents seeking housing or experiencing housing issues) with patience and compassion while respectfully keeping conversations efficient.

Additional Core Requirements:

• Experience: Prior experience in an Executive Assistant, Chief of Staff, or high-level administrative role, ideally within property management, real estate, or a related professional services environment.

• Strategic Execution: Demonstrated ability to go beyond routine admin work to execute high-level strategic, operational, and cross-functional tasks independently.

• Meeting Representation: Ability to exercise sound judgment and professionally represent the executive in calls and meetings during on-site property visits.

• High Volume & Attention to Detail: Comfortable managing high volumes of digital documentation, bank statements, and email correspondence with strong prioritization skills.

• Proactivity & Initiative: Self-starter with high accountability, capable of operating independently, solving problems proactively, and driving open items to completion without constant supervision.

Tech Stack

• Microsoft Office Suite: Excel, PowerPoint, Outlook

• Claude

• Yardi

• Communication & Video Conferencing: Zoom, Teams, Phone/Email

• Standard Calendar and Email software