Chicago Principals & Administrators Association

What Chicago Principals & Administrators Association does

The Chicago Principals & Administrators Association (CPAA) is Local 2 of the American Federation of School Administrators (AFSA) and operates as a professional association and labor union representing school principals, assistant principals, and other school administrators in the Chicago metropolitan area. Founded in conjunction with AFSA in 1975, CPAA is headquartered at 542 S. Dearborn St., Suite 400, in downtown Chicago and operates with a small staff of approximately 9 employees.

CPAA's core offerings are organized as a portfolio of member benefits rather than a unified technology product. These include advocacy representation before school boards and governmental bodies, a legal hotline, professional liability insurance (provided via AFSA), an AFSA Legal Action Trust that provides up to $25,000 in defense cost coverage for constitutional, 'failure to educate,' and criminal matters, annual professional development through the Illinois Administrators' Academy (mandatory for Illinois licensure), and supplemental insurance programs including long-term care, dental, and accidental death and dismemberment coverage. The organization also operates a Political Action Committee (CPAA PAC) and participates in the APEX coalition for broader public education advocacy. Distribution is primarily through the website (chicago.theschoolleader.org), a members-only portal (mycpaa.org), social media channels (Twitter, Facebook, Instagram, YouTube), and partnerships with AFSA, the Illinois Administrators' Academy, Union Plus, and CSA Local 1.

CPAA's business model is membership-dues-based subscription revenue, with members paying periodic dues in exchange for the bundle of advocacy, legal, professional development, and insurance benefits. The organization does not own proprietary technology systems and offers no AI/ML capabilities, software products, or APIs; its technology footprint is limited to standard web and social platforms. CPAA operates under the strategic umbrella of parent organization AFSA, which provides national advocacy infrastructure, insurance programs, and legal resources, while CPAA focuses on Chicago-specific needs such as CPS budget advocacy and elected school board accountability.

Name

Chicago Principals & Administrators Association

Legal name

Chicago Principals & Administrators Association

Website

https://mycpaa.com

Company type

Private

Founded year

1975

Operating status

Operating

Headcount range

1–10 employees

Short description

The Chicago Principals & Administrators Association is Local 2 of the American Federation of School Administrators, a Chicago-based professional association and labor union representing school principals and administrators through advocacy, legal services, professional development, insurance benefits, and political action.

Ownership category

akta.pro rank

Product category

Education Union and Professional Association Services

NAICS

Professional Organizations (81392), Professional Organizations (813920)

SIC

Services-Membership Organizations (8600)

akta.pro primary industry

Professional Development / CPD Requirement Administration for Licensure (EDADAJAL)

akta.pro secondary industry

Education Professionals (Teacher/Administrator CE, CPD) (EDAAALAE)

Keywords

• Education union services
• School administrator advocacy
• Professional development licensing
• Educator legal protection
• Membership association benefits

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Others

Revenue model

1. Membership Dues: The organization operates as a professional association (Local 2 of the American Federation of School Administrators) and generates revenue through membership dues from school principals and administrators in the Chicago area. Members pay periodic dues in exchange for advocacy representation, professional development resources, legal hotline access, insurance benefits, and other member services.

Go-to-market motion1 record

Distribution channels3 records

Marketing channels7 records

Core offering

CPAA is a professional membership association and labor union (Local 2 of the American Federation of School Administrators) that provides school principals and administrators in the Chicago area with professional advocacy, legal protection services, professional development courses, insurance benefits, and political representation. Members pay dues to access the CPAA Legal Hotline, AFSA Professional Liability Insurance, the AFSA Legal Action Trust, Illinois Administrators' Academy courses, and a range of supplemental insurance and travel benefits.

Product overview

The Chicago Principals & Administrators Association (CPAA) is a professional membership organization providing a portfolio of member benefits rather than a unified technology product. The core offerings include advocacy programs, legal services (Legal Hotline, Professional Liability Insurance, Legal Action Trust), professional development through the Illinois Administrators' Academy, and various insurance benefits (AFSA Benefits, Voluntary Benefits, Long Term Care, Dental, AD&D). Additional member services include the CPAA PAC for political advocacy, AFSA Travel Programs, and the APEX coalition for public education excellence. These services function as standalone membership benefits offered to school administrators rather than an integrated software platform.

Differentiator

Problem solved

Functional benefit

Products and services

• CPAA Membership Core membership offering for school principals and administrators in the Chicago area. Members gain access to advocacy representation, legal protection, professional development, insurance benefits, and political representation through CPAA and its parent organization AFSA.
• CPAA Legal Hotline Legal consultation service providing members access to legal advice and guidance on matters related to school administration.
• AFSA Professional Liability Insurance Protection for working members in good standing in case of unfavorable judgment in lawsuits naming members as parties or defendants.
• AFSA Legal Action Trust Provides up to $25,000 of coverage for defense costs associated with denial of constitutional rights, 'failure to educate' and criminal charges arising from school activities.
• Professional Development (Illinois Administrators' Academy) Annual professional development courses required for Illinois school leaders to maintain their administrative licenses.
• AFSA Benefits Platform Comprehensive benefits portal providing access to insurance policies, including Long Term Care, Dental, and Accidental Death and Dismemberment coverage for AFSA members.
• AFSA Voluntary Benefits Voluntary supplemental benefits including guaranteed acceptance insurance with no medical questions, exams, or blood tests required.
• CPAA Political Action Committee (PAC) Political advocacy program enabling members to participate in advocacy efforts and hold elected board members accountable.
• AFSA Travel Program Travel programs developed in partnership with Council of School Supervisors and Administrators (CSA), Local 1, offering vacation opportunities worldwide.
• APEX (Allies for Public Education Excellence) Coalition for public education advocacy focused on educational excellence and accountability.

Segments1 record

Ideal customer profiles1 record

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

Five partnerships are on record, tiered core and minor.

• American Federation of School Administrators (AFSA)coreStrategic or Co-development PartnerCPAA operates as Local 2 of AFSA, the national federation representing school administrators. This partnership provides access to national advocacy resources, professional development frameworks, insurance programs, legal resources, and the broader network of school leader locals across the country. AFSA provides the umbrella structure while CPAA focuses on Chicago-specific needs.
• Illinois Administrators' AcademycoreStrategic or Co-development PartnerThe Illinois Administrators' Academy provides mandatory professional development courses required for school administrators to maintain their Illinois teaching licenses. Every school leader must complete an Illinois Administrators' Academy course once a year to maintain licensure.
• Council of School Supervisors and Administrators (CSA), Local 1minorStrategic or Co-development PartnerCSA Local 1 partnered with AFSA to develop AFSA Travel, a travel program offering members vacation opportunities around the world. This partnership provides travel benefits to CPAA members.
• Union PlusminorGTM or Marketing PartnerUnion Plus is a program that provides discounts and benefits to union members. CPAA members gain access to Union Plus benefits as part of their membership package.
• APEX (Allies for Public Education eXcellence)coreStrategic or Co-development PartnerAPEX is a coalition focused on advocating for public education excellence. CPAA participates in this alliance to build broader community support for public education and amplify the voice of school administrators on policy issues.

Scale indicators1 record

Recent moves6 records

Expansion highlights4 records

Broad incumbents

• National Association of Secondary School Principals (NASSP): National association for middle and high school principals; NASSP provides parallel leadership development, advocacy, and member services to CPAA's secondary-level members at a much broader geographic scope.
• National Association of Elementary School Principals (NAESP): National professional association serving preK-8 principals across the US; NAESP overlaps with CPAA's advocacy and PD mission but operates at national scale and is not union-structured.

Regional players

• Illinois Education Association (IEA): Statewide NEA affiliate representing Illinois educators including administrators; IEA is a broader regional peer that competes for the same Illinois school-leader membership pool that CPAA addresses.
• Association of California School Administrators (ACSA): Statewide professional association for California school administrators; ACSA mirrors CPAA's advocacy, PD, and member-benefits model at much larger scale, serving as a regional template for state-level administrator associations.
• Chicago Teachers Union (CTU): AFT-affiliated labor union representing Chicago Public Schools teachers rather than administrators; CTU is a regional peer within the same CPS labor ecosystem with comparable collective bargaining and political advocacy functions.

Direct peers

• American Federation of School Administrators (AFSA): National parent federation of which CPAA is Local 2; AFSA directly provides the insurance programs, legal resources, and national advocacy infrastructure that CPAA distributes to its members, making it the most structurally comparable peer.
• Illinois Principals Association (IPA): Statewide professional association for Illinois school principals; IPA competes directly for the same Illinois administrator members that CPAA serves, offering parallel advocacy, professional development, and networking services at the state level.
• Council of School Supervisors and Administrators (CSA), Local 1: NYC-based Local 1 of AFSA representing school administrators; CSA is a direct peer that co-developed the AFSA Travel Program with CPAA and serves a comparable constituency (urban public-school administrators) with similar advocacy, legal, and PD services.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights5 records

Customer concentration

• Xx.com/ChiPrincipals
• YouTubeyoutube.com/AFSAUnion
• Facebookfacebook.com/ChicagoPrincipals
• Instagraminstagram.com/ChiPrincipals
• LinkedInlinkedin.com/company/mycpaa

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Chicago Principals & Administrators Association