It takes one to know one. Attorneys want to be sold legal tech by people who understand their specific business needs—and who understands the practice of law better than another lawyer? But while there are legal practitioners who are interested in abandoning the trappings of firm or corporate life for a shot at selling legal tech, it's not always a smooth transition. 

"I've seen this play out probably not as successfully as people would like," said Dean Gonsowski, chief revenue officer at ActiveNav and a former litigator.

Nevertheless, he's received "a lot" of outreach over the years from attorneys who wanted to leave the practice of law and were drawn to sales by the promise of a "hot" e-discovery market. And in return, some legal tech companies may see an opportunity to improve their customer outreach.