Jake Cronin

Founder & CEO Siro

Last Reviewed: September 24, 2026

Executive Summary

Jake Cronin is the founder and CEO of Siro, a New York company building AI conversation intelligence for people who sell in person: at the kitchen table, on the job site or in the showroom. Conversation-intelligence tools for video calls became common because video meetings are easy to record. Siro’s argument is that the far larger volume of face-to-face selling has gone uncaptured. Its mobile app records those conversations and uses AI to transcribe and analyze them for coaching. Cronin founded the company in 2020. His own route into business began with selling Cutco knives door to door as a college student, and he later worked at McKinsey. Siro raised a $50 million Series B led by SignalFire in 2025 and reports $75 million in total funding.

Career Highlights

• Founded Siro in 2020 and leads it as Founder & CEO, per the company’s own team page.
• Raised a $50 million Series B in May 2025, led by SignalFire with 01 Advisors, StepStone Group, CRV, Fika Ventures and Index Ventures.
• Grew Siro to $75 million in total funding and hundreds of customers in home improvement, med spas and wholesale distribution, according to the company.
• Earlier worked as a Cutco sales representative, which the company describes as a “top Cutco rep” role, and at McKinsey.

Professional Journey

Cronin’s route into business started in field sales. In his letter announcing the Series B, he writes that at 18, as a college student looking for extra money, he sold Cutco kitchen knives. He says the job taught him how to communicate, handle rejection and bet on himself, and that in-person sales can change the trajectory of someone’s life. Siro’s press materials describe him as a former top Cutco rep and a McKinsey alumnus. They do not give his role or tenure at McKinsey.

He founded Siro in 2020 with a mission the company states as making in-person sales “the most accessible path to financial freedom”. The product is a mobile app. A rep records a sales conversation in person, and Siro’s AI transcribes it, analyzes it and surfaces coaching opportunities and the behaviors associated with closing. The underlying thesis is about data. Virtual meetings produce recordings by default, while in-person conversations have disappeared as soon as they ended, so the field sales workforce has had none of the coaching tooling that inside sales teams take for granted. Siro’s early customers were largely in home improvement, and it has since expanded into med spas and wholesale distribution.

In May 2025 Siro raised a $50 million Series B led by SignalFire, with new investors 01 Advisors and StepStone Group and existing backers CRV, Fika Ventures and Index Ventures. The company said the money would go into product development and into hiring across engineering, sales and customer success. It now reports $75 million in total funding. Its leadership team includes a chief revenue officer and general managers for automotive and new verticals, which suggests the company is organizing itself industry by industry. Siro also describes itself as powering conversation intelligence for ServiceTitan’s Field Pro product.

Education

No institution was named in any source consulted for this profile. Cronin has written that he was a college student when he began selling for Cutco, but the college is not identified.