Career Opportunities

Old St. Mary's School is a National Blue Ribbon PK-8 Catholic School located in the vibrant South Loop of Chicago.  We are seeking motivated, collaborative individuals to join the OSM Team.  As positions become available, they will be posted here.  Instructional positions will also be posted on the Archdiocese HR website.  OSM does not discriminate against qualified applicants on the basis of race, color, gender, age, creed, national or ethnic origin, sexual identity, religion or disability.

OSM is now interviewing for the following positions. 

Teaching Candidates

Associate Principal

Director of Giving

For more information, please click the link above for the Archdiocese HR Website.​

Teaching Candidates

Status: Full-time

Old St. Mary's School is seeking innovative teaching candidates for the 2021-22 school year! OSM is a 2019 National Blue Ribbon Elementary School located in the vibrant South Loop of Chicago, serving 500 students PK-8th grade. We offer a collaborative work environment with endless opportunities for professional growth. Interested candidates should email a resume to Principal Diana Smith dsmith@osmschool.com​​

Director of Giving

Status: Part-time

Join the Old St. Mary’s (OSM) School team during a time of exciting momentum under the leadership of seasoned, dedicated, and talented academic professionals and a strong community of lay leaders.  We have an opening for a Director of Giving responsible for the strategic development, engagement and recognition of individual, business and corporate donor relationships. 


The Director of Giving will develop and manage programs to meet OSM School fundraising goals and serve as liaison to build relationships and engagement with parents, alumni, , parishioners, neighbor businesses and OSM friends with potential to make gifts. This position requires a coordinated approach to the stewardship of donors across the Old St. Mary’s School and Old St. Mary’s Parish community.  


The primary focus for the OSM School Director of Giving position is to:

  • Work with the OSM Principal, with direction and guidance from the OSM School Board and Financial Vitality Task Team to set and achieve OSM School fundraising and engagement goals. 

  • Develop, manage, and execute giving strategies and tactical programming to support a culture of giving. This may include, but is not limited to: annual fund appeal, events, major gifts, planned and legacy giving, strategic partnerships with business and corporate supporters, etc. 

  • Build relationships with and increase engagement of the OSM community of alumni, parents, families and friends via diversified programs and activities to steward relationships.

  • Use best practices and knowledge to improve stewardship and giving practices across the OSM community.

  • Provide high-level support and consultation on gift documentation, tax and legal issues related to charitable giving, gift acceptance and other giving policy-related functions.

  • Perform other related work as needed.


Preferred Competencies 

  • Outstanding interpersonal and communication skills, characterized by the ability to listen, to speak, and to write well with a strong commitment to stewardship and engagement 

  • Excellent organizational skills, and a high degree of flexibility and initiative 

  • Demonstrated skill and knowledge of, or ability to learn quickly, the internal workings of the Old St. Mary’s School and Parish community

  • Ability to work collegially and collaboratively with a diverse team of School and Parish staff, teachers and volunteers


Preferred Qualifications: 
  • Progressively responsible stewardship/development experience or progressively responsible experience in a closely related field such as not-for-profit management or corporate development

  • Demonstrated track record of organizing successful fundraising or marketing activities 

  • Demonstrated success in prospect identification, relationship building, strategizing and solicitation of gifts

  • Experience managing volunteers 

  • Experience at a complex institution, preferably academic or religious

  • Experience developing and monitoring budgets

Please send a letter of interest and resume to Principal Diana Smith, dsmith@osmschool.com.

Elementary Associate Principal

Status: Full-time

Old St. Mary’s School is seeking an associate principal for the 2021-22 school year, effective July 1, 2021. OSM is a Catholic elementary school located in the South Loop of Chicago, serving 500 PK-8th grade students.

Salary and Benefits

The salary and benefits for this position are commensurate with the Archdiocese of Chicago Salary Schedule, with significant opportunities offered for professional and personal growth.

Position Description

The Associate Principal serves on the OSM Administrative Team, and supports the principal’s efforts to further the goals of the OSM Pastor and the Strategic Plan of the OSM School Board. This position is focused primarily on supporting teaching and learning in a faith-based and inclusive environment where all students, families, and staff are welcome. OSM administrators are expected to follow the Leadership Standards established by the Archdiocese of Chicago:


  1. Leading the Catholic Vision/Mission of the School

  2. Leading and Managing Continuous School Improvement

  3. Improving Teaching and Learning

  4. Creating and Sustaining a Culture of High Expectations

Position Responsibilities include but are not limited to:

● Curriculum Implementation

● Professional Growth Coordination

● Instructional Supervision and Support

● Teacher Evaluation

● Recruitment of Instructional Staff

● Assessment Coordination

Please send a letter of interest and resume to Principal Diana Smith, dsmith@osmschool.com.