Anagnost grew up in Van Nuys, California and initially dropped out of high school.^[3] After issues with legal and educational authorities, his family helped him enroll in a new high school and he went on to graduate.^[3] Afterwards, Anagnost went on to earn a bachelor's degree in mechanical engineering from California State University, Northridge (CSUN) in 1987.^[4] His mother, sister, and brother also graduated from CSUN.^[4] During his bachelor's degree, Anagnost completed an internship at Lockheed Martin.^[3] He later obtained an MS in engineering science and a PhD in aeronautical engineering with a minor in computer science from Stanford University.^[5]

Following graduation from his bachelor's, Anagnost initially worked as a composites structure engineer and propulsion installation engineer at Lockheed Martin, where he had previously interned.^[3][6] He left the position to pursue his further education at Stanford, leading to a position at the NASA Ames Research Center as a National Research Council post-doctoral fellow.^[6] Finding the aeronautics business 'too slow', he joined the Exa Corporation in Boston in 1992, before joining Autodesk as a product manager in 1997.^[7]

Early on in his career at Autodesk, he led development of the company’s manufacturing products and increased the revenue of Autodesk Inventor five-fold to more than $500 million.^[5][8] Working his way up through the company over the years, he achieved the position of Chief Marketing Officer and SVP of the Business Strategy & Marketing. In these roles, he was credited with Autodesk's transition to software as a service, as well as the adoption of cloud computing.^[5][8]

Following the resignation of Carl Bass, Anagnost was appointed as interim-CEO together with Amar Hanspal, the Chief Product Officer.^[1] Following a four month search, Anagnost was permanently appointed as President and CEO of the company.^[1] In this role, Anagnost has pushed for a refocus of the company on software for construction, leading to the demise of some other company ventures and a workforce slash which saw 1,200 employees lose their job at the company.^[7] As part of the new focus, Autodesk acquired construction tech start-ups PlanGrid for $875 million, the company's biggest ever acquisition, and BuildingConnected for $275 million in 2018.^[9] Additionally, since becoming CEO, the company's share price has nearly tripled and Autodesk has reached a market value of $41.1B, entering the Forbes Global 2000 and Fortune 500.^[7][10][11]

Growing up, Anagnost's dream job was to work on space ships for NASA.^[12] He enjoys reading science fiction novels, with The Fountains of Paradise being one of his favorite works, and is a fan of both the Star Wars and Star Trek franchises.^[12]

In 2018, Anagnost was one of the judges in the Annual Engineering Showcase at his alma mater CSUN and hosted a talk at the university.^[13][14] The following year he was rewarded with the 2019 Distinguished Alumni Award from CSUN.^[15] That same year, Anagnost and his wife donated $300,000 to the university to establish the Teresa Sendra-Anagnost Memorial Scholarship Endowment in honor of his mother, who died in 2011 after suffering complications from cardiac surgery.^[4] The endowment supports outstanding students in the university's College of Engineering and Computer Science through funding of their education.^[4] Autodesk also donated $1 million to CSUN in 2020 to support the founding and construction of a Center for Integrated Design and Advanced Manufacturing at the university.^[16]