Jake Cronin

Jake Cronin is the founder and CEO of Siro, a New York based conversation intelligence platform that records and analyzes the face-to-face conversations of field sales reps and turns them into AI coaching. He learned the sales craft the hard way, selling Cutco knives door to door as a teenager and ranking among the company's top reps worldwide, then spent two years as a McKinsey business analyst before leaving in 2020 to code Siro's first product himself. The company has raised roughly $75 million, including a $50 million Series B led by SignalFire in 2025, and works with home services, telecom, and multifamily sales teams across the country.