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      City Year

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      Senior Director, Development Interview

      17 Oct 2025
      Anonymous interview candidate
      No offer
      Neutral experience
      Average interview

      Application

      I applied online. The process took 4 weeks. I interviewed at City Year

      Interview

      The interview process moved quickly, but in hindsight highlighted several red flags. From the beginning there seemed to be confusion around what role I was most suited for, as I initially applied for a separate role on the team. The following interviews clarified some questions about the full scope of the position, and I was invited to an in-person interview in Chicago. Meeting with the current team members was a positive experience and I enjoyed speaking with executive leadership, as well-- however about ten minutes into the conversation it was made clear that utilizing the board for any type of fundraising was essentially off the table. Soon after my confusion grew as exec leadership pushed the need to qualify and cultivate new donors/new gifts instead of focusing on stewarding current major donors... at that point they lost me. All in all - the mission remains noble and the impact is real -- the fit was just not there and I withdrew my application. Further, I was disappointed to see the original role I applied for had been filled before my final interview as I was told my focus on the senior director role would not undercut my chances for the original role. Oh well.

      Interview questions [1]

      Question 1

      What are specific places in the city to meet, qualify, and cultivate new major donors?
      Answer question