Before joining VenueNext, DeMillo was CTO of StudioNow, a video production marketplace. Prior to StudioNow, Rob was the CTO of Discovery Digital Networks which he came through via Discovery's acquisition of the Internet Television company, Revision3. In 2013, DeMillo was named to Econtent’s “Fabulous 15: The Top Digital Media Influencers” along with Steve Jobs, Jeff Bezos and Mark Zuckerberg. DeMillo has been both the CTO and founder of several companies over the last 20 years, including Transpera (acquired by Tremor Media), Third Screen Media (acquired by AOL), m-Qube (acquired by VeriSign where he served as SVP of Mobile Technology), and served as SVP of Engineering at Art Technology Group as the company was taken public.

In addition, DeMillo is a Venture Partner at Sparklabs Global, a South Korean incubator/accelerator, where he mentors fledgling companies in SLG's portfolio.

Before he became a serial entrepreneur, DeMillo was a research scientist/engineer at Lincoln Laboratories, and Jet Propulsion Laboratories before that, applying technology to study and understand topics as diverse as planetary cratering and effects of microbursts on aircraft.