Executive Assistant to the Superintendent

Milford Public Schools•Milford, CT

1d•Onsite

About The Position

Milford Public Schools is seeking an Executive Assistant to the Superintendent. This is a full-time, 12-month, non-union position that reports directly to the Superintendent of Schools. The Executive Assistant will provide high-level, confidential support to the Superintendent, acting as a strategic partner in managing the Superintendent's office and coordinating with other departments and school buildings. This role demands exceptional discretion, independent judgment, and the ability to manage complex situations with minimal supervision in a high-pressure environment. The position offers administrative assistance and management support requiring a high degree of awareness, tact, creativity, and initiative in directing or completing projects and resolving problems.

Requirements

High school diploma or equivalent (e.g., GED, college, technical/trade school transcript, or foreign credential equivalency).
Minimum of five (5) to seven (7) years of experience in an executive-level administrative role involving extensive public contact, preferably within a school system, municipality, or complex corporate environment.
At least three (3) of those years must have included supervisory experience overseeing staff and/or projects, along with responsibility for organizing, coordinating, and performing duties at a high level of independence.
Highly proficient with standard office and productivity software and digital collaboration tools, including Google Workspace (Calendar, Docs, Drive, Sheets, etc.), Microsoft Office Suite (Word, PowerPoint, Outlook, Excel), and the ability to quickly learn additional district-specific platforms (e.g., student information systems, board management software).
Demonstrated ability to remain calm, organized, and effective during high-demand periods, such as budget development and the start of the school year.
Strong time-management skills, with the ability to manage multiple tasks simultaneously and prioritize based on importance and urgency.
Must provide documented evidence of training and experience sufficient to satisfy the above qualifications.

Nice To Haves

Knowledge of school district operations, organizational structure, and governance processes.
Knowledge of public records laws (e.g., Freedom of Information Act/state open-records requirements) and procedures for managing and responding to records requests.
Knowledge of District policies, procedures, and applicable legislative/regulatory compliance requirements.
Extensive knowledge of personal computers and standard software applications, including word processing, databases, spreadsheets, and presentation tools.
Strong writing and editing skills, including accuracy in spelling, punctuation, grammar, and formatting.
Strong verbal and interpersonal communication skills.
Meticulous attention to detail and superior organizational skills in managing complex, multi-faceted projects and competing priorities.
Leadership and supervisory skills, with the ability to guide and direct the work of subordinate staff.
Ability to plan, organize, and prioritize work, and to work independently with minimal supervision.
Ability to maintain confidentiality and exercise sound judgment and discretion, including in the handling of sensitive correspondence involving staff, parents/guardians, legal counsel, and the Board of Education.
Ability to interpret and apply written and oral instructions, procedures, and regulations.
Ability to gain cooperation and compliance from others without direct authority.
Ability to determine appropriate courses of action for unique or unprecedented situations, and to recognize when to act independently versus when to refer matters to administrators.
Ability to meet deadlines and adapt quickly when priorities shift.
Ability to build and maintain positive relationships with staff, management, outside agencies, and the public, using tact and diplomacy.
Ability to work flexible hours as needed.
Ability to recognize safety hazards and apply safe work practices.

Responsibilities

Manages the internal operations of the Superintendent's office, providing high-level administrative, analytical, and coordination support.
Serves as a key point of contact for the public, staff, and board members—responding to inquiries, interpreting district policies and procedures, and resolving issues independently when possible, escalating appropriately when needed.
Plans, organizes, and oversees the daily administrative and clerical operations of the Superintendent's office, supervising support staff to ensure smooth workflow and service delivery.
Manages the Superintendent's calendar, prioritizing competing demands across board relations, site visits, community events, and district emergencies.
Provides administrative support during emergency situations or crisis communications (e.g., school closures, safety incidents), helping coordinate rapid information flow.
Prepares board meeting agendas, compiles supporting materials, and drafts related reports for submission and board review.
Maintains official district records, including board policies, meeting minutes, and resolutions, ensuring accurate archiving and retrieval.
Conducts research and independently compiles, analyzes, and summarizes data (financial, statistical, and narrative) to support district operations, special projects, and administrative decision-making.
Establishes and implements procedures that carry out operational policies, applying knowledge of district programs, policies, and procedures.
Coordinates and tracks the progress of projects, initiatives, and committee work; arranges and supports meetings and conferences as directed.
Reviews outgoing materials for accuracy, formatting, consistency, and proper approvals prior to administrative sign-off.
Uses standard office and productivity software (word processing, spreadsheets, presentation and data-visualization tools, and district information systems) to prepare correspondence, reports, and statistical materials, and manage digital scheduling and communication.
Attends meetings to provide agenda preparation and minute-taking/transcription support.
Maintains strict confidentiality regarding student records, personnel matters, and sensitive district information in accordance with FERPA and other applicable state/federal regulations.
Processes and coordinates responses to public records requests (e.g., FOIA/state open-records law) in coordination with legal counsel as needed.
Supports district communication with parents, community members, and media inquiries, routing sensitive matters to appropriate administrative staff.
Maintains familiarity with relevant education code, school law, and board policy to ensure correspondence and procedures align with legal requirements.
Contributes to performance evaluations of assigned support staff.
Adheres to safety standards and other duties as assigned.