In 1990, Hailpern joined the Technical Strategy Development Staff in IBM Corporate Headquarters (Armonk, New York) returning to the Research Division in 1991, where he served as senior technical consultant to the Research Division and vice president for systems and software.
In 2004, he became the department group manager for software technology, where, as director of programming models and tools, he managed departments researching programming technology, software engineering, and tools for non-programmers.
He moved to the research center in San Jose in October 2011, as director of computer science.
He retired from IBM at the end of 2019 and currently works as a professor for the Silicon Valley satellite campus of Northeastern University.
Hailpern has authored many publications[2] and United States patents,[3] along with numerous conference papers and book chapters.
[12] Hailpern was a trustee of the Katonah-Lewisboro Union Free School District from July 2002 to June 2005.