At the end of this school year, Anne Hobbs, Director of Development and Alumni Relations, will retire after 31 years at Latin. When Ms. Hobbs joined the fundraising team in 1991, she was only the fifth team member. Since then, the department has doubled in size. Her children, both lifers, graduated from Latin in 2016 and 2017, as well as from college, and it is now time for Ms. Hobbs to “graduate,” too. She said that the decision is “entirely personal.” She said she plans to spend time with her parents, traveling, and reading.

During Ms. Hobbs’ three decades of service and leadership, Latin’s development efforts have grown from simply focusing on annual giving to an office that works with all groups within the school and all the Latin constituencies. She is especially proud of Latin’s “extensive alumni program.”

Even after 31 years, Ms. Hobbs still enjoys her work. She is quick to point out that the work isn’t and wasn’t always glamorous. During her tenure, she has pulled several all-nighters, ordered and arranged for more porta potties than she can count, and often executed superhero-like costume changes in the bathroom to be ready for meetings and events.

She says she has laughed and learned a lot, but when she looks back on her three decades here at Latin, what is Ms. Hobbs most proud of?

Not just her fundraising, but “how the fundraising has enhanced the experience of the school.” She is especially proud of how her team’s work helped provide for a separate Middle School building as well as providing support to allow full day kindergarten, and how it supported the creation of the fifth floor Upper School classrooms.

Additionally, she is proud of how her department’s work supports the school’s partnership and close work with High Jump. High Jump provides tuition-free academic enrichment for Middle School students of diverse backgrounds and of limited economic means from schools throughout Chicago. Yet the most important accomplishment, treasured personally by Ms. Hobbs, are “the relationships [she] has developed over the course of time at school.”

Ms. Hobbs told a story about how longtime former Latin employee Mary Ann McFarlane helped show her the ropes. Ms. McFarlane retired just before Ms. Hobbs started. Ms. McFarlane would call Ms. Hobbs with unannounced pop quizzes during Hobbs’ first few years at school. Ms. Hobbs unsuspectingly would pick up the phone, and Ms. McFarlane would throw out an alum’s name, randomly. Ms. Hobbs’ job was to then tell Ms. MacFarlane what year the alum graduated. Ms. Hobbs chuckled and explained that if she failed, “She’d scold me, saying that if I was going to represent Latin and work with alumni, I had to know who they were.” Ms. Hobbs took Ms. McFarlane’s admonition to heart, and with determination and intentionality, she and her team have grown alumni participation in volunteerism and financial participation from 6 percent to 20 percent over the past 30 years.

Assistant Head of School Shelley Greenwood is grateful for Ms. Hobbs’ years of dedicated work. “Anne Hobbs was one of the first people I met when I came to interview for an opening at Latin in 1993. Fast forward 30 years and she remains one of my favorite colleagues of all time,” Ms. Greenwood said. “Anne taught me everything I know about development and alumni relations.”

Hobbs points out that her biggest challenge is that it isn’t obvious or easy to see how much work goes into fundraising, development, and alumni relations. She pointed out that “the impact of our work isn’t very well-known.” Ms. Hobbs feels that “there is a false impression” that Latin doesn’t need significant philanthropic and volunteer involvement. Ms. Hobbs would like more people in the Latin community to know that Latin is “very dependant as a school on the impact of volunteerism and philanthropy to provide the school experience.”

Ms. Greenwood understands this impact. “Look around Latin,” said Ms. Greenwood. “Whether it is a new cutting-edge curricular initiative, a state-of-the-art teaching and learning space or a vibrant board of trustees, Anne has had a hand in all of this and so much more.”

There also was the false impression, even by Ms. Hobbs, that her job would be more, as she put it, “fancy.” One of her favorite stories is about when she first interviewed at Latin. Ms. Hobbs thought Latin “would be super fancy,” but she said that when they interviewed her, her chair for the meeting was two stacked boxes. Ms. Hobbs feels that experience captures what is for her, the real culture of Latin and her job; it is about the student experience, not something unimportant like the chair you sit on.

Ms. Hobbs would like to spend her last year focusing on programs that are about the student experience. She wants to make the most of this year, being back in person after the disruption of COVID-19. She is focused on “returning to the pattern and cadence that we weren’t able to enjoy during the pandemic.” She is looking forward to being able to interact directly, face to face, with alumni, parents, and students.

When asked how students can help with her work, Ms. Hobbs was thankful for that question. “I would love to hear more about your experiences, more about what you hope for in terms of the school’s development.” She said that direct feedback from students is very important to establishing priorities for her office and that students are always the best way to thank alumni for their participation.

“I will miss Anne,” said Ms Greenwood. “We all will. We are better because of her dedication to our school.”