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How iMentor Chicago partnered with Prosper Strategies to find their focus, articulate their vision for the future and set themselves up for fundraising success.

The Challenge


When iMentor Chicago first engaged with Prosper Strategies, they were at a crossroads. The mentorship organization had spent the last five years building a foundation for success in Chicago and forging partnerships with four Chicago Public Schools. As they looked toward the next five years, they decided they were ready to commit to doubling the number of schools and tripling the number of students they serve. But before they could begin to scale, iMentor Chicago needed to figure out how to articulate their vision, differentiators and reason for being in a way that would compel more supporters to invest in their growth. They also needed to determine who would be most likely to support them financially so they could focus their development efforts on the right donors and foundations and develop a solid case for support that would help them reach their $22 million fundraising goal.

Prosper Strategies used elements of the Nonprofit Impact System™  to address these challenges. After discovering a compelling reason for being for iMentor Chicago, we built a new messaging platform for the organization, conducted deep research to determine who their target donors should be, and created a case for support for their $22M fundraising campaign.


We began our work with research intended to help us uncover information that would guide our approach to this work. We conducted an organization assessment focused on a review of iMentor Chicago’s current marketing, communications and fundraising materials, an ecosystem assessment focused on comparing iMentor Chicago to other similar mentorship and  higher ed access organizations in Chicago, and a stakeholder assessment that included stakeholder focus groups and a deep dive into donor data on ResearchPoint.



Research revealed that the iMentor Chicago’s reason for being should center around the fact that they are the mentorship organization best positioned to advance racial equity in Chicago. No other organization in their ecosystem focuses on reciprocal mentorship, works with every student within a school (not just the highest performers), and recognizes post-secondary pathways other than four-year college. This combination of factors give iMentor a unique opportunity to address issues of education equity and racial disparities in access to post-secondary pathways.

With iMentor Chicago’s reason for being solidified, we moved on to developing a new messaging platform for the organization. We used two messaging frameworks – one to set up the problem the organization exists to address and one to describe how iMentor Chicago is solving it. We also created messaging themes iMentor staff could use when developing communication and fundraising collateral or in conversations with prospective donors and supporters.



iMentor had a strategic plan in place, but they needed Prosper’s help with several aspects of their fundraising strategy, such as:

  • Financial modeling to determine how to position their fundraising goals
  • Foundation and corporate partner targeting research to determine which groups would be most likely to support iMentor’s growth financially
  • Donor profiling to determine who was giving to other, similar organizations and help iMentor target the right donor prospects

After working with them on all of the above, we developed a creative way to talk about and visualize iMentor’s $22M growth goal. We also developed a list of target foundations,  corporate partners, and target individual donor criteria they could use to target digital advertising, direct outreach and more. iMentor then incorporated each of these elements into their master fundraising strategy.



Engaging both internal and external stakeholders was an important part of our process with iMentor. We developed a committee of internal staff members who provided feedback on our work every step of the way, as well as a project taskforce of both internal and external stakeholders (donors, board members, program participants, etc.) who reviewed key deliverables, such as the reason for being and case for support, and provided feedback. Throughout this process, our goal was to make sure that iMentor was representing the people the organization exists to work with in a strength-based manner that felt true to their lived experience.



In partnership with staff, we worked to ensure that the strategy we had built would be realized. First, we worked with iMentor to develop their case for support. Then, we provided guidance to the organization’s CEO and Director of Development on using their new reason for being, key messages and donor targets in the real world, and helped them build the systems, processes and measurement dashboard necessary for ongoing fundraising and communications success.



This work was just finalized in February 2020, so results will not be available until later this year. iMentor Chicago is currently on track to meet their $22M five-year fundraising goal.

“Everything we did with Prosper exceeded my expectations. It was all clearly based in research and strategy. Plans were well laid out and easy to follow, giving us a clear vision for our work. We also have the ability to reference and update these materials for years to come. We are so excited to launch our new campaign concept this year as well as our new donor acquisition programming.”

– Carey Kogol, Director of Development, iMentor Chicago

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