Oliver Jacobi ’05: Former Windward Student, Now Senior Underwriter at Multinational Insurance Company

This article originally appeared in The Beacon Spring 2016 issue.

When The Beacon approached Windward alumnus Oliver Jacobi ’05 for an interview, it was hard not to be impressed by his email signature when he responded: Senior Underwriter at AIG—one of the largest insurance companies in the world. Oliver Jacobi ’05 has accomplished much since being identified, at 6-years old, with language based learning disabilities. After attending Prospect Hill Elementary School in Pelham, N.Y. in his kindergarten year, he was accepted into The Windward School and began first grade on the Windward Avenue campus.

Upon graduating from Windward in 2005, Oliver went on to attend The Pennington School, where he boarded for two years. The college preparatory school was a perfect transition for him because, along with classes in English and math for students with dyslexia, it also offered honors and advanced placement classes to suit his intellect and abilities. By sophomore year, Oliver was excelling in math and was encouraged to transition into the standard curriculum courses at Pennington.

“The main reason I went there was for English and math,” Oliver says. “From an educational standpoint, I didn’t think it was necessary to stay at Pennington if they were moving me into regular classes.”

From Pennington, Oliver went to Pelham High School. “I had never. attended public school and wanted to experience that,” he explains. He was glad to finally go to school with his hometown friends, and it was helpful knowing that Pelham had resource rooms for dyslexic students. By graduation, three years later, Oliver was well equipped for the next step. He headed to Skidmore College in Saratoga. N.Y. and majored in Business Management.

“Academically, the small class sizes at Skidmore were perfect for me,” he says. “In addition, the college’s business curriculum was well-rounded. Along with finance classes, I studied HR and entrepreneurship.”

Upon graduation, Oliver moved to San Diego and had a brief job as a valet.

He soon achieved his broker’s license and entered a training program with AIG. A year-and-a-half later, Oliver was offered a position in San Francisco. Transferring to New York, though, was always in his game plan.

After returning East, Oliver assumed his current position as a senior property and causality underwriter at AIG in Manhattan. He assesses multi-million dollar risk insurance for high-end net worth individuals by personalizing the process and reviewing insurance possibilities for their homes, cars, jewelry, and fine art.

It is a challenging role with significant responsibilities. “My job relies mostly on math, salesmanship, and my ability to work with others,” he explains. Although his position does not rely heavily on writing, Oliver readily admits that it takes him longer than many of his colleagues to write reports for his manager.

Last February, Windward teacher Ms. Plotycia, whose son was Oliver’s good friend in high school, coordinated a return visit for Oliver to talk to the eighth and ninth graders about life after Windward and all that the School had done for him.

Over lunch in the Westchester Middle School conference room with eight students on the cusp of transitioning to mainstream schools, Oliver shared how understanding his learning differences helped in high school and college as well as in deciding on a career. He paused to note how impressed he was with the growth of Windward.

“When I was here, we were a small school on Windward Avenue. Now, with a new campus in Manhattan, The Windward School is like an empire,” he said. “This growth reflects the excellence of the school and how the public perception about dyslexia has changed.”

Oliver reassured the students by recognizing that going to a mainstream high school can be “… nerve-wracking, especially if you’re dyslexic and starting out as ‘the new kid.’ I was lucky when I returned to Pelham because I already had a group of friends. Socially I wasn’t really ‘the new guy,’ but I understand how you might be feeling right now.”

“It was great to have Oliver back on campus,” says Chris Eberhard, Head of Westchester Middle School and Oliver’s former homeroom teacher. “He is a wonderful young man who left Windward with the confidence and skills to determine his fate in the working world.”

Oliver credits Windward teachers for doing a great job at building students’ confidence. “Some of the biggest things I learned were knowing my weaknesses and strengths, and the importance of organization. I keep my schedules together and my room organized so that I don’t feel flustered. This has helped me in my work life with trying to prioritize different projects and keep things neatly filed so I know where they are.

“Windward also instilled in me the great habit of proofreading, whether it is for a long referral to my boss or just a social email or text to friends. I’m always re-reading what I write.”

Oliver carries this ingrained sense of organization into his personal life.

“I try to stick to plans that I set up, whether short-term or long-term. I think this is a good character trait,” he says. “My friends like to tease me for being overprepared, but it’s a good skill to have. Many people have trouble sticking to calendars and being organized. I am definitely proactive with always knowing what my upcoming schedule is.”

“Windward teachers are very patient,” Oliver recalls. “They know even better than the students that, just because you’re dyslexic, doesn’t mean you can’t be successful or cope with life,” he continues. “The teachers were always kind in building students’ courage and self-esteem.

“A lot of students at Windward might be struggling with reading or writing, but many have extraordinary talent in other areas,” Oliver concludes. “In one way, they have an edge on people outside of Windward because they see the world differently.”