Full-Time

Director of Head Start and Early Head Start

The Opportunity Alliance

The Opportunity Alliance

201-500 employees

Nonprofit community action agency delivering integrated services

Compensation Overview

$85k - $95k/yr

+ 403(b) retirement match + Tuition reimbursement

South Portland, ME, USA + 2 more

More locations: Westbrook, ME, USA | Portland, ME, USA

In Person

Office is based in South Portland; travel to classroom locations in Portland, South Portland, and Westbrook may be required.

Bachelor's, Master's

Category
Education
Required Skills
Word/Pages/Docs

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Requirements
  • A Master's degree in Early Childhood Education or a related field, or a bachelor's degree in Early Childhood Education; alternatively, a bachelor's degree in a field related to Early Childhood Education with coursework equivalent to a major in Early Childhood Education and at least five years of experience in a managerial role involving program planning, operations, and evaluation.
  • At least 3-5 years of supervisory experience is required.
  • Demonstrated group facilitation skills and experience leading and engaging parents.
  • Strong verbal and written communication skills, along with computer and word processing skills.
  • Sensitivity and familiarity working with diverse populations.
  • Ability to pass a pre-employment physical and tuberculosis screening.
  • Early Childhood Education staff must have current measles, mumps, and rubella and tetanus, diphtheria, and pertussis immunizations.
  • Ability to pass criminal background, child protective services, and sex offender checks.
  • Must not be on a state or federal suspension and disbarment list.
  • Ability to exert moderate physical effort, including occasional standing, walking, reaching, stooping, bending, kneeling, crouching, and typing, and to frequently lift and carry children or materials weighing up to 25 pounds.
  • A valid driver's license or driving ability may be necessary to attend meetings and trainings.
Responsibilities
  • Supervise and manage the overall operations of the Head Start and Early Head Start program.
  • Ensure service design, delivery, and quality comply with federal Head Start Standards, state licensing regulations, and all legal and contractual obligations.
  • Set expectations for program managers and hold them accountable for achieving specific child and family outcome results.
  • Evaluate and improve program systems.
  • Represent the agency in local, regional, and state communities.
  • Plan and make decisions within the framework of the organization's mission, values, and goals.
  • Work primarily during regular business hours from Monday through Friday, with some evening hours as needed.
  • Support classrooms across Portland, South Portland, and Westbrook, with travel to classroom locations as required.
Desired Qualifications
  • Computer and word processing skills are preferred.
The Opportunity Alliance

The Opportunity Alliance

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The Opportunity Alliance is a non-profit community action agency serving Cumberland County, Maine, coordinating programs to help individuals and families build stable lives. It uses a wrap-around, holistic approach across four pillars—Behavioral Health & Wellness, Community Well-Being, Childcare & Early Childhood Education, and Poverty & Economic Mobility—with services like Maine Crisis Line/988, 211 Maine, residential treatment, homelessness prevention, heating assistance, Head Start, and WIC. It is funded by grants, public funding, and donations, and it uses data-driven, trauma-informed care to measure impact and ensure quality. Its goal is to reduce poverty, increase stability, and create economic mobility for people and communities, with statewide reach for some programs and deep local roots dating back to 1965.

Company Size

201-500

Company Stage

N/A

Total Funding

N/A

Headquarters

South Portland, Maine

Founded

1965

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Simplify Jobs

Simplify's Take

What believers are saying

  • The Office of Head Start awarded TOA $13.3 million through June 30, 2028.
  • TOA's crisis infrastructure stays relevant as Maine expands 988 and community-based response.
  • Partnerships like Hannaford and Lake Region High School's 2025 food closet broaden TOA's reach.

What critics are saying

  • TOA settled federal and Maine claims on May 23, 2025 over drug-testing reimbursement.
  • The Provider Labs case exposes compliance weakness across Medicaid billing and vendor oversight.
  • A major federal grant expires June 30, 2028; Head Start funding loss would cripple operations.

What makes The Opportunity Alliance unique

  • TOA runs Maine Crisis Line/988 statewide, answering 3,835 weekly calls in July 2026.
  • It combines crisis, housing, Head Start, and WIC services under one Cumberland County agency.
  • Joseph Everett has led TOA for over two decades, preserving deep local relationships.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

403(b) retirement with a generous agency match (all employees are eligible)

Tuition Reimbursement

Unlimited Paid Time Off

Flexible Work Hours

Remote Work Options

Paid Holidays

Paid Vacation

Family Planning Benefits

Fertility Treatment Support

Professional Development Budget

Conference Attendance Budget

Wellness Program

Mental Health Support

Stock Options

Company Equity

Phone/Internet Stipend

Home Office Stipend

401(k) Retirement Plan

401(k) Company Match

Education allowance

Adoption Assistance

Childcare Support

Elder Care Support

Relocation Assistance

Employee Referral Bonus

Life Insurance

Disability Insurance

Medical benefits

Dental and Vision insurance options