Wobbrock conducts research and teaches in the field of Human-Computer Interaction (HCI) with a focus on input and interaction techniques, human performance measurement and modeling, HCI research and design methods, virtual reality, mobile computing, and accessible computing.

His advisees have gone on to positions at Harvard, Cornell, Colorado, Washington, Brown, Simon Fraser, Amazon, Apple, Google, and Microsoft, among others.

After working in Silicon Valley startups for a few years, he attended the Human-Computer Interaction Institute in the School of Computer Science at Carnegie Mellon University, where he earned his Ph.D. (2006).

His specific research topics include text entry, pointing, touch, and gesture; human performance measurement and modeling; HCI research and design methods; virtual reality; mobile HCI; and accessible computing.

Some of his notable research projects are the $-family gesture recognizers,[14] the end-user elicitation design method,[15][16] the Slide Rule design for accessible touchscreen gestures[17] (which some have noted might have influenced Apple's VoiceOver accessibility software design[18]), the ARTool statistics tool[19][20] for nonparametric ANOVA-type analyses, the Pointing Magnifier assistive pointing and visual aid,[21][22] and the versatile EdgeWrite text-entry system.

This massive open online course (MOOC) focuses on experiment design and data analysis in the R programming language for formal Human-Computer Interaction studies.

Wobbrock was the venture-backed cofounder and CEO of AnswerDash, a SaaS startup that provides intelligent in-context help to websites and mobile apps.