The Wentcher Foundation

Managing Directors of Programs

Position Title: Managing Director of Programs

Reporting to: Executive Director

Start Date: mid-September

Location: Downtown Chicago

Role Type: Hybrid In-Person

Priority Application Deadline: August 21

Organization Overview

Founded in 1997 by successful business leader and entrepreneur, Ernest Wentcher, the Wentcher Foundation has grown dramatically from a small program serving a handful of scholars into one of the largest scholarship providers in Chicago supporting nearly 400 students and awarding $3.2 million annually across three programs. The Foundation’s mission is to create equitable educational opportunities for high-achieving Chicago-area students by ensuring they earn a college degree and go on to positively impact their communities. The Foundation has committed $23 million in funding to more than 1,000 exceptional Wentcher scholars and achieved a remarkable 93% college graduation rate since inception. Learn more about our impact, history, and programs here.


Key Responsibilities

The Managing Director of Programs (MDP) is a senior leadership role responsible for the management and execution of our scholarship programs. The MDP plays an essential role directing scholar selection and supports to ensure the long-term success of Wentcher Scholars, from initial application through college graduation. The MDP will be a highly organized, data-driven leader that enjoys the big picture and is equally passionate about managing the details so important tasks do not fall through the cracks. In addition, the MDP will be responsible for implementing and strengthening existing program systems to meet or exceed Foundation goals in collaboration with the entire team. Likewise, the MDP will be a persuasive communicator skilled at building authentic relationships with a wide range of stakeholders. The ideal candidate for the MDP is a passionate, student-centered leader with a track record of leveraging data to drive program excellence and an understanding of how to maximize scholarship awards to avoid displacement. This role reports to the Executive Director and will collaborate with the entire Foundation team and Board of Directors.

Major areas of responsibility include:

Program Leadership & Management (40%)

  • Lead and manage the annual scholar selection process – from program promotion to prospective students through application submission, finalist interviews, and awardee selection.
  • Actively monitor and track scholar academic performance and make recommendations on scholar renewal status
  • Lead communications to prospective and current scholars, families, and high school leaders regarding important deadlines and expectations
  • Manage, develop, and support the Program Manager with meeting key deadlines and goals
  • Model and cultivate a strong culture of collaboration, communication, and two-way feedback
  • Contribute to strategic planning efforts regarding future program growth and development

Manage & Strengthen Program Elements to Drive Efficiency & Impact (25%)

  • Lead efficient and effective program operations through implementation of application and support systems in collaboration with Foundation staff, scholars, volunteers, and vendors
  • Evaluate and enhance existing program elements to strengthen the overall scholar experience
  • Monitor and evaluate the effectiveness of third-party support providers (Chegg, Perspectives)
  • Collect and analyze program data along with scholar feedback to track program outcomes and trends over time
  • Synthesize program analysis and outcomes into reports for the Executive Director and Board of Directors

Build Authentic and Long-term Relationships with Strategic Partners (25%)

  • Identify opportunities and take action to cultivate meaningful connections with a wide range of stakeholders including scholars, Foundation staff, high school leaders, financial aid offices, nonprofit partners, and other strategic partners
  • Treat all scholars, staff, and partners with respect, integrity, humility, and empathy
  • Actively seek and share feedback openly with scholars, staff, and partners
  • Maintain strong relationships with key partners through timely communication and reports

Organizational Support (10%)

  • Support planning and execution of special events throughout the year
  • Lead and manage special projects aligned to the Foundation’s long-term strategic plan
  • Represent the Foundation at key meetings and events to increase visibility for its mission and programs


Job Requirements & Qualifications

  • Work Authorization and Bachelor’s degree; Master’s degree (preferred)
  • Minimum of 10 years of professional experience working across the following sectors: K-12 or higher education, college access, persistence, & success, financial aid, scholarship management, education philanthropy (or other equivalent)
  • Minimum of 3-5 years of experience in a director level role leading a team (preferred) ▪ Unwavering commitment to Wentcher Foundation’s mission and the students it serves
  • Highly skilled and committed to supporting first-generation, students of color from low-income communities
  • Authentic leader with exceptional communication and interpersonal skills; Fluent in Spanish (preferred)
  • Extremely organized, detail-oriented, and data-driven
  • Proven ability to analyze data to identify trends, influence decisions, and achieve goals
  • Highly skilled at building and managing partnerships to achieve long-term goals
  • Experienced at partnering with Chicago Public Schools and Board of Directors (preferred)
  • Highly skilled at Microsoft 365 applications (Teams, Excel, SharePoint, Outlook, Word, PowerPoint) and similar web-based tools
  • Demonstrated ability to manage and leverage databases to create efficient workflows and drive program results
  • Able to constructively influence other team members by setting priorities and expectations, adhering to deadlines, measuring results, and maintaining optimism in the face of adversity


Hybrid Work Schedule & Travel

Foundation staff are expected to work from our downtown office 3 days a week from 9-5pm. Expected local travel will include meetings and visits to high schools and universities as well as periodic out of state travel to universities with a critical mass of Wentcher Scholars.



The Wentcher Foundation provides its staff members with a competitive salary and comprehensive benefits package. The expected salary range for this role is $125,000 – $135,000. Foundation benefits include medical, dental, and vision insurance, 401(k) retirement plan with 4% match, 33 days of paid time off (20 vacation and 13 paid holidays), and an extensive set of voluntary benefits.


Application Process

Interested candidates should submit a professional cover letter detailing their qualifications and updated resume to Priority will be given to applications submitted by August 21, 2023.

As an equal opportunity employer, the Wentcher Foundation does not discriminate against any employee or applicant based on race, color, religion, national origin, age, gender, sex, ancestry, citizenship status, mental or physical disability, sexual orientation, veteran status, or military status. The Wentcher Foundation invites and strongly encourages applications from people of all backgrounds.