Positions Available:



Job Description:

Shepherds Mission and Values

Shepherds is a 25-year-old non-profit organization based in Bridgeport, Connecticut, whose mission is to close the educational opportunity gap for underserved high school students in Connecticut. Founded in 1998, Shepherds’ motto is “Changing Lives…One Student at a Time.”  When Shepherds was first founded, the goal was to improve high school graduation rates among inner city high school students in the Fairfield County area. Having grown from just five students in the first year, Shepherds now serves over 60 students each year in the Bridgeport and New Haven communities.  Over 350 students have graduated through our program with the opportunity to attend institutions of higher learning.

The Shepherds approach involves a three-pronged strategy. First is providing financial support for students to attend a private four-year college preparatory high school. Second is providing academic, college prep and life skills workshops in addition to various experiences designed to prepare students for college and the adult world.  The last and most important element is providing each student with the guidance and encouragement of a volunteer adult mentor during their four years in high school.

Position Summary

The Shepherds’ Executive Director (“ED”) is the organization’s leader with responsibilities that span across all strategies and functions of the organization. Working closely with our Board of Directors, the ED’s primary responsibility is to build and run the organization’s team and the varied functions that support and implement the strategic objectives of the Board. Responsibilities include but are not limited to:

Lead the Shepherds team to effectively implement their respective jobs.
Represent Shepherds to the larger community of school partners, volunteer mentors, donors, students, and the student’s respective family members.
Assure both the short-term and long-term financial stability and integrity of the organization to ensure that the organization can fulfill its mission including a variety of fund-raising activities.
Work with our partner schools, staff, and board members to identify qualified students who will be enrolled in our freshman class each year.
Identify and constantly improve the quality and relevance of the services, programs, and support that we deliver to our students.

Skills & Attributes

Strong collaborative management skills to lead a small team of dedicated and skilled professionals.
Excellent writing and speaking skills to effectively communicate with the organization’s constituents that range from 14-year-old high school students and their family members to peer professionals, volunteers, and trustees of large foundations.
Strong sales and marketing skills would enable the successful candidate to build community awareness, open doors, and maximize opportunities with both our volunteers and donors.
With the oversight and guidance of the board treasurer, the ED acts as the organization’s CFO preparing the budget and using the organization’s accounting systems to continually monitor and analyze Shepherds’ financial position, so some financial education/experience is necessary.
The ability to build relationships across all of Shepherds’ constituencies is important for making mentor referrals and finding new funding connections.
The successful candidate must be flexible and have good problem-solving skills.

Education and Experience Required

Minimum educational requirement for this position is a bachelor’s degree.
A graduate degree or comparable professional experience would be very helpful in the areas of sales/marketing, business/finance or education.
A proven track-record of success in leading and running an organization (not necessarily a non-profit) would be valuable.
Prior experience on a non-profit board(s) or committee(s) in the Fairfield or New Haven area is helpful. Likewise, knowledge of the Fairfield and/or New Haven philanthropic landscape is a plus.
Any prior experience which would be indicative of a candidate’s willingness to be committed to the Shepherds’ mission such as experience as a volunteer in a related area such as after-school academic support/tutoring, Big Brother/Big Sister program, or similar program(s).

Compensation and Benefits

This is a full-time position.
Shepherds’ principal offices are located on the campus of our Bridgeport school partner, Kolbe Cathedral High School.
Working in-office is expected but there is some flexibility depending on work demands, time of year, etc. The board’s Executive Committee will continually evaluate this policy to ensure that the organization is running effectively.
Compensation for this position is commensurate with the candidate’s skills, experience, and ability to contribute from the start.
Benefits information is available by request from the Shepherds’ Search Coordinator.

Please contact Carrie Sindelar with questions or to be considered for this position.  jsindela@yahoo.com or (203) 984-7171.



Location: Kolbe Cathedral High School, Bridgeport, CT
Part-time (three - four days per week, with flexibility)

Job Description:
Shepherds (shepherdsmentors.org), a 24-year old non-profit, is seeking a mission-driven, educational professional with a range of interpersonal skills and experience and demonstrated initiative to perform a critical role in our small and thriving organization. Shepherds’ mission is to close the educational opportunity gap and provide the foundation for success for underserved high school students in Connecticut.

Reporting to the Executive Director (ED), the Shepherds Liaison to Kolbe Cathedral High School (KCHS) role will take a highly visible and responsible role representing Shepherds among the KCHS Shepherds community of students, mentors, and parents. The person will also work closely with other members of the Shepherds’ team and the administrative, academic and guidance staff at KCHS. The role is essentially both an ambassador for Shepherds to the school community and a mentor for our two most important communities- students and mentors.

The goal of the position is to enhance the success of the Shepherds’ program among students, families and Shepherds mentors at KCHS. This will include but not be limited to,

  • Monitoring and helping guide the academic progress of the students towards graduation,
  • Supporting healthy and active student-mentor relationships, i.e. being the first point of contact between mentors and students,
  • Directing and administering a program of academic, social and life skills enrichment programs appropriate for Kolbe Cathedral Shepherds students.

As an integral member of the Shepherds team, the Shepherds KCHS Liaison provides valuable insight and input to Shepherds’ strategies and programs, communicates issues and ideas to Shepherds management and staff and participates in important decision making.

What is Shepherds?
Shepherds’ motto is, “Changing Lives… One Student at a Time.” Shepherds provides three key services to achieve its’ mission: tuition support for academically qualified and ambitious young people to attend a non-public high school in their local community, college prep and career programming, and an adult mentor for four years.

As of April 2023, there are 61 Shepherds students in our two partner college preparatory high schools, 41 in Bridgeport and 19 in West Haven. Our offices are in Bridgeport on the campus of KCHS. Given the nature of the work with students, school staff and faculty, mentors and the importance of communication with Shepherds’ colleagues, this role will primarily be performed on-site, with limited work from home time.

Some of the specific responsibilities include:

  • Facilitate the screening and selection of new students each year with KCHS Admissions
    Organize and run new student and mentor training programs
  • Monitor grades, school behavior, mentor-student interaction to assure academic and Shepherds standards are being met; intervene with plans for improvement as needed
  • Coach and guide mentors on effective mentor principles and problem solving
  • Direct and supervise the initiation and scheduling of supplemental academic and life skills programs and student-mentor events throughout course of year
  • Network to find mentors and sponsors for new students.

Specific requirements include:

  • Minimum of a Bachelor’s degree; graduate degree in education helpful
  • Prior experience in high school education as a teacher, guidance counselor or similar position,
  • Familiarity with a broad range of academic and life skills fields to support supplemental activities,
  • Personal qualities of integrity, credibility, and a commitment to and passion for Shepherds’ mission.

Time Commitment:

This role will require approximately 18 - 24 hours per week (three 6-8 hour days; four 5-6 hour days) during the academic year and less time during the summer months. There will be increased demands on the person’s time in the fall launch of the new school year, during mid-year programming activities, and in the spring for end of year events.

Competitive and commensurate with the candidates experience and breadth of skills. Hours will vary over the course of the year as events and priorities demand. Liaison will be paid as an independent contractor and will be provided a Form 1099 at year’s end; no benefits are part of this arrangement.

Inquiries may be directed to info@shepherdsmentors.org. Include a copy of your resume or CV.