Leadership Development Trainer Jobs (NOW HIRING)

PLEASE NOTE THAT PURSUANT TO MASSACHUSETTS GENERAL LAW, CONTRACTED EMPLOYEES ARE NOT PAID FOR THE TWELVE SCHEDULED HOLIDAYS, DO NOT RECEIVE ANY PAID, VACATION, PERSONAL LEAVE BENEFITS, OR CONTRIBUTE TO THE STATE RETIREMENT SYSTEM OR SOCIAL SECURITY. AS A STATE CONTRACTED EMPLOYEE, YOU MUST PARTICIPATE IN DIRECT DEPOSIT AND CONTRIBUTE TOWARDS THE COMMONWEALTH OF MASSACHUSETTS STATE ALTERNATE RETIREMENT PLAN, ("OBRA PLAN").

The Department of Elementary & Secondary Education (DESE) is seeking a Leadership Development Contractor to support the Office of Educational Leadership Development's (OELD) Leadership Development, Recruitment, and Retention workstream under the direction of the Director of OELD and Senior Associate Commissioner of Specialized Supports. The Leadership Development Contractor will broadly focus on the following:

       Overseeing and facilitating, where needed, training and support for educational leaders in Massachusetts

       Building leadership pipelines

       Providing coaching and mentoring support for new school and district leaders that will increase retention, especially for leaders underrepresented at each level of leadership

The Leadership Development Contractor is an equity-oriented educator with significant experience and expertise in effectively leading schools and districts. Within DESE, the Contractor will work closely with other DESE staff as needed to ensure alignment and successful implementation of assigned work while ensuring effective delivery of services and support to schools and districts involved in the work. Outside of DESE, the Contractor will have frequent and supportive interactions with school and district leaders, education advocacy groups, and research organizations, within the Commonwealth.

In general, the Leadership Development Contractor will support the development of, in coordination with the OELD Director and the Senior Associate Commissioner of Specialized Supports, and lead the implementation of the following:

       Training and support to further develop culturally responsive school and district leaders

       School and district leadership pipelines focused on leadership diversification, such as Influence 100 for aspiring superintendents and Aspiring Principals Fellowship for aspiring principals

       Alumni engagement efforts and support for Influence 100 alumni

       Professional development, coaching, and mentoring for new school and district leaders

       Working with MASC, MASS and MSAA on training for school leaders, district leaders, and school committees to strengthen leadership decision-making and strategic planning at all levels of leadership

       Supporting vendors with Instructional leadership training for new and current school leaders

       Supporting vendors with Instructional leadership training for new superintendents

       Developing and implementing guidance materials on strategic resource allocation aligned to district goals/priorities and cross-role (school committee, district leaders, and school leaders) budget decision-making frameworks, as well as online modules aligned to those guidance materials and frameworks

       Lead, in collaboration with stakeholders and vendors, a set of professional learning cadres for school leaders that bring together schools from specific regions of the Commonwealth to learn from one another, build their instructional leadership skills, and plans to improve the academic success of their school.

       Perform other duties as assigned

       Based on assignment, travel may be required.

Please submit a cover letter and resume with your online application.

Questions regarding this posting or the application process should be referred to Maureen O'Brien at  Maureen.t.o'brien@mass.gov or 781-338-6107.

The Leadership Development Contractor would also serve as a liaison to the following stakeholder groups:

       Urban Superintendent's Network (USN)

       Massachusetts Association of School Superintendents (MASS)

       Massachusetts School Administrators Association (MSAA)

       Massachusetts Association of School Committees (MASC)

 Below are brief descriptions of three of the main programs/initiatives the Contractor would support the development and lead the implementation of.

 Influence 100 Program

Support the Department's continued planning and implementation of the Influence 100 program. In collaboration with a vendor, the Leadership Development Contractor will support programmatic aspects of the program, which may include, but is not limited to, the development of monthly fellow sessions, quarterly leadership sessions with fellows and district leadership teams, development of a comprehensive coaching model for current fellows, and alumni engagement strategy. The Leadership Development Contractor will design and implement four online sessions with alumnae of Influence 100 to build their readiness to apply for an assistant superintendent position or superintendent position.

Aspiring Principals Fellowship Program

Support the Department's continued planning and implementation of the Aspiring Principals Fellowship program. In collaboration with a vendor, the Leadership Development Contractor will support programmatic aspects of the program, which may include, but is not limited to, the development of monthly fellow sessions, quarterly leadership sessions with fellows and school leaders, development of a comprehensive coaching model for current fellows, and alumni engagement strategy.

Professional Learning Cadres for School Leaders

Support the Department's efforts to develop a new principal leadership development program, with an emphasis on supporting Accelerating Achievement school leaders. The purpose of the program - to be developed and launched during the 2026-2027 school year - is to provide opportunities for school leaders to build and refine their skills through case study reviews, observations, and discussions of effective structures and practices that result in better outcomes for students, especially historically underserved students. Participants would be organized into three regional cadres that would be supported by a leadership coach, creating opportunities for leaders to conduct site visits to one another's schools to reflect collaboratively on effective practices and areas for refinement.

 Minimum qualifications required at hire:

Applicants must have at least (A) 15 years of full-time or equivalent part-time, or equivalent part-time, supervisory or managerial experience in public administration or education management, and (B) of which at least 5 years must have been in a managerial capacity.

 Preferred qualifications:

        A master's degree in education or another relevant field

      Deep knowledge of schools and school districts and how they function across states.

       Demonstrated track record of setting ambitious goals and driving results.

       Energetic, entrepreneurial, and self-motivated with the judgment, temperament and skills required to make strategic decisions based on equity and outcomes for all children.

       Ability to develop high-quality written products, including communication, and presentation skills.

       Excellent relationship builder with demonstrated experience managing change and teams.

       Disciplined, data-driven approach to decision-making and problem-solving.

       Passion for MA DESE's mission.

       Unwavering belief in the ability of all children to learn at high levels.

       Passion for attaining ambitious goals in service of Massachusetts students and educators.

       Efficient and organized; able to coordinate various projects simultaneously.

       Improvement mindset; desire to coach, be coached, receive feedback, and continually improve.

An Equal Opportunity / Affirmative Action Employer.  Females, minorities, veterans, and persons with disabilities are strongly encouraged to apply.

The Commonwealth is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, sex, gender identity or expression, sexual orientation, age, disability, national origin, veteran status, or any other basis covered by appropriate law.  Research suggests that qualified women, Black, Indigenous, and Persons of Color (BIPOC) may self-select out of opportunities if they don't meet 100% of the job requirements.  We encourage individuals who believe they have the skills necessary to thrive to apply for this role.