High School Success Specialist - Bridges

Overview
Bridges is a youth-development program that is committed to the long-term success of Baltimore City youth and to providing life-changing opportunities to independent school students. In the 2025–2026 program year, Bridges will work with 871 young people – 485 Baltimore City youth ages 9–23 and 386 independent school students – through its sites at The St. Paul’s Schools, Gilman School, The Bryn Mawr School, and McDonogh School.

The Opportunity
Bridges is seeking candidates for the role of High School Success Specialist to join the Bridges at Bryn Mawr team. The holder of this role will be hired and employed by The Bryn Mawr School and work with other members of Bridges’ High School, College, & Career Division. Bridges currently works with 86 Baltimore City high school students, and the first cohort of Bridges at Bryn Mawr students will move up to high school at the end of the 2025–2026 school year.

The High School Success Specialist will support the success of Bridges students by taking on four key responsibilities:

1. Student Success Support
   Work with a caseload of approximately 40 students throughout the year. Advising includes meeting individually with students on a monthly basis to discuss and offer support for academic progress, career goals, and development of life skills.

2. Program Planning, Execution, and Enhancement
   Assist with planning, facilitating, and evaluating seasonal enrichment programs. Current programs include after-school tutoring at the Bridges Baltimore office in Belvedere Square, a monthly Saturday Institute (October–May), and a five-week Summer Jobs Program held on campus at Loyola University Maryland.

3. Communications
   Serve as a member of the Bridges News Team and capture photos, videos, and stories for Bridges’ marketing and communications via social media and newsletter.

4. Administrative Responsibilities
   Complete general administrative tasks including attending team meetings, completing divisional reporting and case notes, and communicating with students, families, and others via phone and email.

Ideal Candidates

• Bachelor’s degree

• 1–4 years of relevant work experience (candidates with less or more experience are welcome)

• Experience or interest in working with high school students

• Ability to build strong, culturally competent relationships

• Strong organizational and project management skills

• Optimistic and positive mindset

• Proficiency with workplace technology (email, text, Microsoft and Google Suite)

• Valid driver’s license and reliable transportation

• Spanish language proficiency encouraged but not required

Details

• Compensation: $50,000–$57,500 (based on experience, education, and skills)

• Benefits: Comprehensive benefits package through The Bryn Mawr School, including:

  • Medical, Dental, Vision, HSA, FSA

  • Employee Assistance Program

  • Graduate School/Professional Development funding

  • 403(b) retirement plan with employer contribution and match

  • Legal resources, Aflac, pet insurance

  • Life, accidental death & dismemberment insurance

  • Short-term and long-term disability insurance

  • Paid vacation, sick, and personal leave

• Supervision: Jointly supervised by the Bridges at Bryn Mawr Site Director and the Bridges Baltimore Senior Director of High School, College, and Career Programs

• Start Date: Ideally around June 1, 2026

• Location: Baltimore, MD (primarily in-person with some hybrid flexibility)

• Hours: 40 hours per week, including some evenings and weekends

To Apply

• Email a resume to hiring@bridgesbaltimore.org

• Rolling review; apply by January 31, 2026

• Resume filename format: HSSS – Last Name, First Name

• Email body should include your name, how you learned about the opportunity, and 1–3 sentences summarizing your interest

Bridges Baltimore and The Bryn Mawr School are equal opportunity employers committed to diversity, equity, inclusion, and belonging. Candidates from underrepresented backgrounds are strongly encouraged to apply.