High School Success Specialist

Job Details:
Level: Experienced;

Job Location:

Gilman School - Baltimore, MD 21210;
Position Type:
Full Time;
Education Level: 4 Year Degree;
Salary Range: $50,000.00 – $58,500.00 per year;
Job Shift: Day.

Bridges Baltimore and Gilman School are searching for the next Bridges at Gilman High School Success Specialist. Bridges Baltimore is an organization committed to the long term success of Baltimore City students and to providing life changing opportunities to independent school students. Gilman School is a private independent day school for boys located in Baltimore City. Bridges Baltimore and Gilman School opened Bridges at Gilman in 2014 and the program is now in its 12th year of operation.

The Opportunity Bridges programs support the success of Baltimore City students for 13 years, starting at age 9 and continuing until age 23.

• Student Success Support:
  Working with a caseload of approximately 40 high school students throughout the year. This includes meeting individually with students on a monthly basis to discuss and offer support for academic progress, career goals, and development of life skills.
• Programming:
  Assisting with planning, facilitating, and evaluating seasonal enrichment programs for high school students. Current programs include after school tutoring at the Bridges Baltimore offices in Belvedere Square, a monthly Saturday program (October‑May), and a five‑week summer program held on campus at Loyola University Maryland.
• Communications:
  Serving as a member of the Bridges News Team and capturing photos, videos, and stories for Bridges’ marketing and communications via social media and newsletter.
• Administrative Responsibilities:
  Managing general administrative responsibilities, including representing the division at team meetings; completing divisional reporting and keeping case notes; and communicating with students, families, and others via phone and e‑mail.

• Have a bachelor’s degree.
• Have 1–4 years of work experience in a relevant field with a track record of success.
• Have experience or interest in working with and coaching a high school student population, with comfort and confidence meeting students and families where they are.
• Are able to form strong relationships with a range of people regardless of background and can communicate in a culturally competent manner.
• Have strong organizational and project management skills with the ability to work both individually and with a diverse team.
• Keep an attitude of optimism and positivity in their work.
• Are proficient in workplace technology including e‑mail, text, Microsoft and Google suite, and the ability to adapt to other tools as needed.
• Have a driver’s license and a reliable form of transportation.
• While not a requirement, candidates with proficiency in Spanish language skills are strongly encouraged to apply.

The High School Success Specialist is a full‑time, 12‑month role. The Specialist will be employed by Gilman School within a salary range of $50,000–$58,500. Final salary will be dependent on several factors, including years of experience, education, and skills. The Specialist will also have access to a full and comprehensive benefits package through Gilman School.

Supervision:
This role is supervised jointly by the Bridges at Gilman Site Director and the Bridges Baltimore Senior Director of High School, College, and Career Programs.

Start Date:

We look forward to bringing someone on before the start of the 2026‑2027 school year, targeting late August 2026.

Location:

This role will be based in Baltimore, MD, and requires meetings at various locations in the metropolitan region. The majority of work is in‑person, with some hybrid flexibility to be determined with the role’s supervisors.

Hours:

This 40‑hour per‑week role requires some weekend and evening work. Your 40‑hour schedule will be determined in partnership with your supervisors.

GILMAN SCHOOL is an equal opportunity employer and educator who fully and actively supports equal access for all qualified applicants, regardless of race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability status, Genetic Information or Testing, Family and Medical Leave, protected veteran status or any other characteristic protected by law. We prohibit retaliation against individuals who bring forth any complaint, orally or in writing, to the employer or the government, or against any individuals who assist or participate in the investigation of any complaint, or otherwise oppose discrimination.