He is the CEO of Parchment and a co-founder of Blackboard Inc. Pittinsky is also affiliated with Arizona State University as an assistant research professor.

[8] Pittinsky wanted to become a teacher from an early age,[4][9] though he initially struggled as a student and had to repeat failed classes in summer school.

At the time of the company's foundation, it operated as a consulting group to the IMS e-Learning standards project, where Pittinsky was an early member.

[1][14] In 1998, Blackboard LLC merged with CourseInfo LLC, an online learning software company developed by Cornell University students Stephen Gilfus and Daniel Cane, to create Blackboard Inc.[12][13][15] CourseInfo had already developed a product and found a market fit by selling to 15 premier institutions.

[1] In 2002, while at Blackboard, Pittinsky co-wrote and edited a book called The Wired Tower on e-learning and the internet's impact on education.

[18] Pittinsky and Chasen sold Blackboard to private-equity firm Providence Equity Partners in 2011, following a $2 billion valuation.

[14][20] He was later introduced to Docufide, a company founded in 2003 that specialized in the online transfer of academic transcripts from high schools to colleges and universities.

[25] He has also helped expand Parchment's services to allow users to store and transfer transcripts, use academic data such as test scores and GPA to find matching institutions, and determine their likelihood of acceptance.

[14][20] During his time at Parchment, he became an advocate for the adoption of Postsecondary Achievement Reports (PAR), which are documents that include both traditional academic records, such as grades, and information about student's development and learning experiences.

[5] Active as an angel investor, Pittinsky has invested in companies including SocialRadar, Interfolio,[29] Picmonic,[30] and Stellic.

[34] In addition to Blackboard and Parchment,[35] he has been on the boards of The Institute for Citizens & Scholars (formerly the Woodrow Wilson National Fellowship Foundation),[10][36] CampusLogic, the High Meadows Graduate School of Teaching and Learning (formerly the Woodrow Wilson Graduate School of Teaching and Learning), and Picmonic.