WANTED! The World’s Most Organized, Trustworthy, and Tech-Savvy Executive Assistant

Full Job Description

Who We Are

Montessori Thrive is a mission-driven, fully remote team supporting Montessori school leaders with marketing, enrollment, operations, and leadership systems. We’re partners, problem-solvers, and strategic thinkers who believe schools work best when their leaders are supported by strong systems and clear communication. We collaborate across time zones, communicate openly, and

show up ready to make a meaningful impact every day. If operational excellence energizes you — and you care about supporting a mission that matters — you’ll fit right in.

What We’re Looking For

We’re hiring a full-time Executive Assistant (EA) to serve as the CEO’s right hand. This high-trust role requires exceptional organization, proactive thinking, impeccable communication, and a deep

commitment to confidentiality. You must be comfortable supporting HR workflows, handling sensitive information, and interacting professionally with school owners, CEOs, and high-level partners. This is not an entry-level role — it’s for someone who thrives in a fast-paced environment and takes pride in anticipating what needs to happen next.

Compensation & Growth

Competitive full-time salary

Strong long-term growth potential

Opportunity to evolve into operations leadership or a future Chief of Staff

Who You Are at Your Core

You’re someone who sees what needs to be done and quietly makes it happen. You thrive on clarity, structure, and helping a fast-paced leader operate at their best. You enjoy creating order, improving systems, and supporting a mission that impacts schools and children.

Our Values

Excellence — We deliver clarity and quality in every task.

Community — We respect and support each other and the schools we serve.

Integrity — We communicate honestly and act in the best interest of our clients.

To Apply, Send the following:

When you apply, please make the subject line: “I actually read the instructions.”

Resume in PDF format, named: [Lastname.Firstname.EA.pdf]

Job Responsibilities

Your Core Responsibilities

Communication & Calendar

Manage the CEO’s inbox with strategic prioritization

Draft polished communication and meeting follow-ups

Oversee scheduling, buffers, reminders, and meeting prep

Provide concise summaries, notes, and briefings

HR & Confidential Information

Manage onboarding documents, payroll-related tracking, and personnel files

Maintain secure HR records and schedule performance cycles

Support internal communication discreetly and professionally

Finance & Operations

Maintain spreadsheets for budgeting, expenses, and projections

Track payments, reimbursements, and vendor information

Prepare simple financial summaries and assist with light bookkeeping

Projects & Systems

Manage ClickUp tasks and cross-team workflows

Create templates and systems that improve efficiency

Coordinate in Slack and follow up to keep projects moving

Executive Representation

Interact professionally with school owners, CEOs, and partners

Prepare agendas, talking points, and documents

Anticipate needs, solve problems early, and protect the CEO’s time

Job Requirements

What You Need to Succeed

Skills & Technical Ability

Strong proficiency in Google Workspace

High spreadsheet competency (formulas, dashboards, tracking)

Ability to learn digital tools quickly

Experience with CRMs and project management tools

Comfortable troubleshooting online systems and workflows

Communication

Exceptional English fluency (CEFR C1 or higher)

Polished writing skills and professional presence

Ability to summarize information clearly and concisely

Personal Traits

Trustworthy, discreet, and reliable

Exceptionally organized and detail-oriented

Calm under pressure; proactive in solving problems

Professional, steady, and consistent in follow-through

Preferred Experience

Prior EA or operational support experience

HR or payroll-related experience is a strong plus

Experience supporting executives, founders, or business owners

Remote work experience in a deadline-driven environment

You Must Be Comfortable With

Reliable remote work and a dedicated workspace

Camera-on meetings

Managing multiple priorities at once

Regular feedback and continuous improvement

Completing the CEFR English test (C1+)

A 60-day trial period to ensure mutual fit

Skills Required

• Market Research - Beginner
• Email Management - Expert
• Administration - Intermediate
• Research - Beginner
• Project Management - Intermediate
• Payroll - Intermediate
• Financial Reporting - Intermediate
• Youtube - Intermediate
• Social Media - Intermediate
• Business Communication - Intermediate
• Time Management - Intermediate
• Communication Skills - Expert
• Decision Making - Intermediate

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