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Ask Media Group
Ask Jeeves taught the early web to accept a question in plain English. Three decades later, its corporate descendant became a sophisticated traffic-and-advertising machine - and a case study in what happens when a media business depends on someone else’s search ecosystem.
Maxx Lobo
Maxx Lobo is the Chief Executive Officer of Ask Media Group, the IAC-owned digital media and performance marketing company behind Ask.com and other properties reaching 245 million people monthly. A two-decade veteran of ad-tech, cloud infrastructure, and digital media, Lobo rose through the ranks as CTO and COO/President before taking the top role in 2025. Under his operational leadership, Ask Media Group tripled its EBITDA from $50 million to over $100 million in four years, cementing his reputation as one of the more quietly effective operators in the digital media landscape.