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

OSM Enrollment Director

The OSM Enrollment Director oversees all aspects of admissions, recruitment and financial aid and will direct the admissions process from inquiry through tours through enrollment. The Director will lead a collaborative effort to meet the enrollment objectives for Old St. Mary's School.

The ideal candidate is data-driven and experienced in admissions, recruitment and retention. The Director will lead inclusive outreach efforts to draw diverse families to the school and ensure that OSM continues to enroll promising students who both thrive as part of the school community and in turn contribute to the OSM community. A genuine and empathic communication style is required, along with strong organizational and tech skills. 


Interested candidates should submit a resume and letter of interest to Diana Smith, Principal of Old St. Mary's School

Old St. Mary’s School

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 

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Old St. Mary's School,  1474 South Michigan Avenue, Chicago, Illinois 60605 |  |  Tel: 312-386-1560

 Office Hours: Mon - Fri  7am-3:30pm