David Cutler was born in Lansing, Michigan and grew up in DeWitt, Michigan. After graduating from Olivet College in 1965, Cutler went to work for DuPont. One of his tasks was developing and running computer simulations on Digital machines. He developed an interest in operating systems and left DuPont to pursue that interest.

Cutler's software career started at a small company he founded called Agrippa-Ord, located in Monument Square, Concord, Massachusetts (or possibly in Acton, Massachusetts), marketing software for the LINC and PDP-8 computers.

Cutler holds over 20 patents and is an affiliate professor in the Computer Science Department at the University of Washington.

David Cutler usefully summarised his own career in the foreword to Inside Windows NT.

In addition to his engineering skills, Cutler is known for his sardonic humor. He generally referred to the RSX fork list as the "fork queue" Sometimes even his error messages turn out to have a double meaning.

David is also an avid auto racing driver. He has previously competed in the Atlantic Championship from 1996 to 2002, scoring a career best of 8th on the Milwaukee Mile in 2000.

In April 1975, DIGITAL began a hardware project, code named Star, to design on a 32-bit virtual address extension to its PDP-11. In June 1975, Dave together with Dick Hustvedt, and Peter Lippman were appointed the technical project leaders for the software project, code-named Starlet, to develop a totally new operating system for the Star family of processors. These two projects were tightly integrated from the beginning. The three technical leaders of the Starlet project together with three technical leaders of the Star project formed the "Blue Ribbon Committee" at DIGITAL who produced the fifth design evolution for the programs. The design featured simplifications to the memory management and process scheduling schemes of the earlier proposals and the architecture was accepted. The Star and Starlet projects culminated in the development of the VAX-11/780 superminicomputer and the VAX/VMS operating system, respectively.

At DEC he is widely credited with having terminated the 1979-80 Desktop RSTS project and scrapping the manufacturing prototype. Compared to the subsequently announced IBM-PC, RSTS had 40,000 running applications, ANSI languages, and a DBMS. RSTS had a reputation as a robust, stable and reliable multi-user, multi-tasking operating system. RSTS also had a virtual operating mode that allowed it to faithfully emulate other operating systems such as RSX-11M and RT11.

He was also known for his disdain for all things UNIX. His sardonic nature showed through in the VMS v UNIX debates at DEC in the early 1980s. He would often show his low opinion by referring to the UNIX process I/O model by reciting "getta byte, getta byte, getta byte byte byte" to the rhythm of the "cavalry charge" finale of Rossini's William Tell Overture (made popular as the theme music for the Lone Ranger TV series).

DIGITAL began working on RISC technology in 1986 and Cutler, who was then working in DEC's DECWest facility in Bellevue, Washington, was elected to head Prism, a project to develop the company’s RISC machine. Its operating system, code named Mica, was to embody the next generation of design principles and have a compatibility layer for UNIX and VMS. The RISC machine was to be based on ECL technology, and was one of three ECL projects DIGITAL was undertaking at the time.