Associate Managing Director, Development


The Associate Managing Director, Development is an accomplished development leader with a proven track record of creating and implementing strategies to cultivate donors and multi-million dollar contributions in support of mission-based organizations. Success in this role is dependent on the cultivation of both a strong personal local donor network in Chicago and key national foundations, close coordination with the LEAP Board, and a strategic mindset to identify new revenue-generating channels, including government contracts and grants.

As the leader of the Development team, the Associate Managing Director will build upon the nearly $35 million LEAP has raised to date from incredible local and national donors by helping us meet an ambitious fundraising goal of more than $20 million over the next two years. The Associate Managing Director will also lead the development of a HNWI network, partner closely with LEAP’s CEO and serve as a bridge between LEAP’s mission-based success and external constituents with an interest in the financial health of the organization.


Fundraising Strategy Development:

  • Develop and lead overall fundraising strategy including individual donors, foundations, and government grants that meet LEAP’s annual fiscal requirements.
  • Develop a balanced funding mix of donor sources and solicitation programs tailored to the needs of LEAP that will enable it to attract, retain and motivate donors.
  • Create strategy-aligned short- and long-range fund development plans and programs that support LEAP’s values, mission and overall objectives.

Fundraising Execution:

  • Ensure that philanthropy and fund development are executed with excellence in keeping with LEAP’s mission and growth trajectory.
  • Solicit and secure major gifts, building a national HNWI network and portfolio of repeat large-giving donors.
  • Manage the CEO’s donor portfolio and a personal portfolio (individual, corporate and foundation donors) by communicating in a timely manner and cultivating and building relationships.
  • Oversee the development and writing of foundation, corporate and government proposals and solicitation materials and collaborate with the Marketing/Communications team to develop key messaging, pitch decks, one-pagers, and annual report.

Staff Management:

  • Set goals for performance that align with LEAP’s core values, fundraising strategy and KPIs, and vision and communicate them to direct reports and team.
  • Supervise and mentor development team and ensure appropriate prospect research and follow up is delivered.
  • Organize workflow and ensure that employees understand their duties or delegated tasks. monitor employee productivity and provide constructive feedback and coaching.

Reporting & Systems:

  • Confirm sound fiscal operation of functional area including timely, accurate and comprehensive development of grant/contribution income, expense budgets and reporting.
  • Maintaining accountability and compliance standards for donors and funding sources.
  • Ensure proper benchmarking and evaluation protocols are in place to support fund development.
  • Ensure design and maintenance of process to track donor and prospect records.
  • Inform CEO and Board of Directors on condition of LEAP’s development program and on all important factors influencing it.


The ideal candidate will enjoy working in a dynamic, results-oriented environment where expectations are high for quality and goal achievement within accelerated timeframes. They will have the following:


  • Bachelor’s Degree
  • 10+ years of experience showing progression as a fundraising leader
  • 5+ years of staff supervisory experience
  • Demonstrated record of achievement as a development leader with a track record of success in creating and implementing strategies to cultivate donors and multi-million dollar contributions
  • Proven success personally securing major gifts at the six-figure level and above
  • Demonstrated skills as a financially literate development leader with the ability to serve as an interpreter between LEAP’s financial management team and external audiences
  • Experience in designing and overseeing appropriate fundraising systems, including donor management, research and cultivation, gift processing and recognition
  • Ability to travel outside of Chicago as needed
  • Acute attention to detail and organization skills
  • Demonstrated project management skills
  • Demonstrated comfort with ambiguity
  • Ability to work in cross-functional teams and drive collaborative work
  • Passion for education and meaningful social impact
  • Strong presentation and group facilitation skills
  • Excellent analytical and problem-solving skills
  • Excellent written/visual and oral communication skills


  • MBA or equivalent
  • Membership in a professional fundraising association
  • An understanding of the personalized learning and EdTech space

Compensation: Commensurate with experience. Excellent health benefits, 403b plan, group life insurance and generous PTO.

Start Date: Position currently available.

Application: Phone inquiries are not accepted. Email your cover letter and resume to to apply. Please include position name in the subject line of your email.