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Orest Jacob Pilskalns has held a variety of roles throughout their career. In 1998, they began working as a Software Engineer at Lockheed Martin. In 2004, they began working as a Professor at Washington State University. In 2006, they became the CEO of MapWith.Us. In 2014, they became the CEO of Skyfish, a leader in smart drone technology for reality/CAD modeling of critical infrastructure. In 2016, they took on the role of Research Professor at the University of Montana.

Orest Jacob Pilskalns obtained a Doctor of Philosophy (Ph.D.) in Computer Science from Washington State University between 2001 and 2004. Prior to that, they obtained Bachelor's degrees in Physics and Mathematics from the University of Montana between 1990 and 1996. Orest Jacob also obtained a NSF Innovation Corp certification from the University of California, Berkeley in August 2017, and a Sun Certified Java Programmer certification from Sun Microsystems.