Full-Time

School Leader

Montessori based, Hiring Bonus

Updated on 8/18/2026

Deadline 8/14/27
Endeavor Schools

Endeavor Schools

201-500 employees

Private school network managing tuition-based campuses

Compensation Overview

$70k - $82k/yr

+ $2,000 hiring bonus

Baltimore, MD, USA

In Person

Bachelor's, Associate's

Category
Education
Required Skills
Microsoft Office

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Requirements
  • An Associate of Arts degree, training, and 3–5 years of experience in education may substitute for the preferred bachelor's degree.
  • A minimum of 5 years of experience in a licensed Early Childhood Learning Center is required.
  • Candidates must meet specific requirements set by minimum state standards and/or accreditation.
  • A minimum of 3 years of managerial experience with strong performance results is required.
  • Proficiency with technology and software applications, including the current version of Microsoft Office, is required.
  • Ability to occasionally lift or move up to 50 pounds is required.
Responsibilities
  • Provide day-to-day leadership to the school serving toddler through elementary-aged learners.
  • Inspire positive community interactions and ensure quality care and education for all children.
  • Foster and develop educational environments and staff.
  • Facilitate implementation of Montessori pedagogy in a safe, healthy, and nurturing classroom environment.
  • Support each child's social, emotional, and intellectual growth and development.
  • Create a family-focused environment that encourages school-community growth.
  • Provide timely feedback, coaching, and development opportunities for staff.
  • Rally teammates around a shared vision and provide motivation and support to reach shared objectives.
  • Collaborate with parents, colleagues, and community partners to provide seamless support for students.
  • Communicate with parents, students, staff, and leadership in a sensitive, honest, empathetic, direct, and professional manner.
  • Align priorities with key business objectives and mobilize resources to maximize return on time invested.
  • Maintain a calm, positive, and professional demeanor during challenges and adversity.
Desired Qualifications
  • A Bachelor’s Degree in Education is preferred.
  • Experience in Montessori education is strongly preferred but not required.

Endeavor Schools builds and runs a network of private schools by acquiring and managing existing private institutions and integrating partner schools into a shared network, while preserving each school’s unique educational philosophy. The schools operate locally and charge tuition to families, with oversight to maintain safety, student well-being, and development. Unlike others who may run schools under a single centralized model, Endeavor combines centralized standards and support with local autonomy, letting each school keep its own traditions while meeting common safety and quality benchmarks. The company aims to provide trusted, high-quality education that fits local communities and supports lifelong learning for children.

Company Size

201-500

Company Stage

Early VC

Total Funding

$14M

Headquarters

Miami, Florida

Founded

2012

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Simplify Jobs

Simplify's Take

What believers are saying

  • Endeavor added Happy Valley Child’s Kingdom in Oregon on August 27, 2025.
  • Endeavor added Living Montessori in Bellevue and Mission Montessori in San Francisco in 2026.
  • The company crossed 100 schools in 2023 and still lists 307 2026 openings.

What critics are saying

  • Revelio estimates headcount fell 6% since 2023, signaling tougher staffing economics.
  • A June 2026 investor suit against Endeavor and Silver Lake reached litigation.
  • Child-safety incidents can trigger parent withdrawals, enrollment losses, and brand collapse.

What makes Endeavor Schools unique

  • Endeavor acquires local brands while preserving Montessori and community-specific philosophies.
  • Its 2026 acquisitions span Oregon, Washington, California, Maryland, and Denver.
  • The school-acquisition playbook formalizes diligence, re-licensing, and operational integration.

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Benefits

Relocation Assistance

Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

4%

2 year growth

3%
PR Newswire
Sep 12th, 2022
Endeavor Schools Expands To San Francisco With Acquisition Of Mission

With its expansion to San Francisco, Endeavor Schools is ensuring that more California families will have the opportunity to give their children a highly effective and enriching Montessori education from one of the top Montessori providers in the country. Endeavor Schools has expanded its California presence by acquiring Mission Montessori, a highly regarded Montessori school serving infants through Elementary-aged children in San Francisco

PR Newswire
Jul 21st, 2022
Endeavor Schools Expands In North Carolina With Two Schools In Raleigh...

With the addition of two Cranfield Academy campuses in Morrisville and Cary, Endeavor Schools now owns and operates 77 schools across the country, including four in North Carolina. Endeavor Schools is continuing its rapid expansion by acquiring two new schools in the Raleigh, North Carolina area

PR Newswire
Jun 28th, 2022
Endeavor Schools Acquires Montessori School In Downtown Baltimore

With campuses in Baltimore’s bustling neighborhoods of Locust Point and Canton, The Baltimore Montessori has been a popular choice for young families for more than 15 years. Endeavor Schools is proud to announce the acquisition of The Baltimore Montessori, an acclaimed school with two campuses in the downtown Baltimore vicinity

PR Newswire
Nov 16th, 2021
Endeavor Schools acquires Village Green Day School

Endeavor Schools has acquired Village Green Day School in Great Falls, Virginia, adding to its growing family of schools across the United States.