Full-Time | $50,000 Health Benefits Extended Vacation | Reports to: Paul Romani (Director)
About Us
Pear Tree School is a progressive private school on a mission to transform education through purpose-driven, hands-on learning. We empower students to discover their calling, develop purpose, and make a real difference in the world.
Our Culture
At Pear Tree School, we are passionate about building a workplace where collaboration, integrity, and continuous learning are at the heart of everything we do. Our team is united by a shared commitment to progressive education and fostering meaningful relationships with our students, families, and community. We prioritize ownership, transparency, and purpose in how we work and lead. If you're someone who values personal growth, innovation, and making an impact, you'll feel right at home here.
The Opportunity
We're looking for an Executive Administrative Assistant who thrives in a dynamic environment and is passionate about supporting visionary leadership. In this role, you will work closely with the school's founders---primarily the Director---to streamline their operations, manage their calendars and inboxes, and provide high-level administrative support that enables them to focus on strategic priorities.
You'll take ownership of both recurring and project-based tasks that are critical to the leadership team's effectiveness. This is a high-trust role with broad visibility across departments.
What You'll Own
1. Executive \& Leadership Support
- Manage personal and professional calendars and appointments for Paul and Alexis.
- Triage and manage their inboxes, prioritizing high-impact communications and flagging action items.
- Coordinate internal and external meetings, including logistics, agendas, and follow-ups.
- Draft and organize reports, presentations, and communications for leadership.
- Anticipate leadership needs and act as a liaison with internal and external stakeholders.
- Protect leadership's time and energy by prioritizing incoming requests and filtering distractions.
- Take ownership of recurring admin processes, enabling leadership to focus on high-level initiatives.
2. Administrative Operations
- Organize project documentation, digital files, and workflows.
- Take ownership of recurring administrative processes.
- Bill payments.
- Scan and file receipts.
- Download and file invoices and bank statements.
- Deposit bank cheques.
- Payroll coordination.
What We're Looking For
- 2 years in an Executive Assistant, Administrative Assistant, or office management role.
- Track record of excelling in fast-paced, high-responsibility environments.
- Excellent communication skills, emotional intelligence, and discretion.
- Experience using AI tools to enhance productivity, automate tasks, and improve communication.
- A proactive, solution-oriented mindset with an appetite for continuous learning.
- Highly proficient with Google Workspace and other digital productivity tools.
Why Join Us
- $50,000 starting salary extended health and dental benefits
- 8 weeks of paid vacation (aligned with the school calendar)
- 3 paid personal days
- Work directly with visionary leaders and make a tangible impact on a growing, mission-driven organization.
- A strong, values-driven culture where you are trusted, empowered, and encouraged to grow.
Future Growth Potential
This role has rapid grow potential for higher-level opportunities such as Senior Executive Administrative Assistant (Senior EAA), Executive Business Partner (EBP), or Chief of Staff (CoS) depending on your skills and aspirations.
Reporting Structure
You'll report directly to Paul Romani (director), ensuring clear alignment, mentorship, and ownership of your role.
Probationary Period
Includes a 3-month probationary period to ensure strong alignment with role expectations and culture.
