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Home » Siro lands $50M to expand its AI-powered coaching for sales reps

Siro lands $50M to expand its AI-powered coaching for sales reps

GTBy GTMay 22, 2025 TechCrunch No Comments3 Mins Read
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An increasing number of meetings have an AI note-taker present that transcribes the call and provides action items. Siro wants to do the same for sales folks who are on the ground and talking to customers face-to-face.

The company on Wednesday announced it has secured $50 million in a Series B round led by SignalFire with participation from Dick Costolo and Adam Bain’s VC firm 01 Advisors. Square CPO Saumil Mehta; the founders of business management software Squire, Songe LaRon and Dave Salvant; former Yelp SVP of Engineering Michael Stoppelman; and former Snap Engineering VP Ding Zhou also participated.

To date, Siro has raised a total of $75 million.

Founder Jake Cronin’s idea for Siro came from an experience in college. For a summer, he had the option of working at an amusement park or selling kitchen knives door to door. He chose the latter and earned good money from it. The next year, he opened an office to hire other sales reps and have them sell knives. But he realized that he couldn’t be on the ground to help coach all the junior reps.

Siro founder Jake Cronin.Image Credits:Siro

A few years later, after working at McKinsey, Cronin started building Siro — coding the core product himself.

“When I was running the knives sales office, I realized a lot of sales work is manual, and good software could have a lot of value,” he told TechCrunch in an interview. “The more I researched sales, I thought that the biggest opportunity here is not in data enrichment or customer relationship management, but it is in improving the lives of sales reps who are on the ground.”

Siro transcribes sales meetings via an app. Features include a company-wide dashboard where sales folks can submit successful calls and sort them by engagement from peers, allowing other reps to listen to top calls and get insights about improving on-ground sales visits.

Image Credits:Siro

Cronin said that Siro trains models for specific industry verticals — for example, for HVAC sales coaching. The company also uses a general-purpose model to gauge how a salesperson is building rapport and handling rejections.

Wayne Hu, a partner at SignalFire, said that the VC firm always wants to invest in companies that have a strong business advantage in data for particular segments.

“Siro’s solution is helping digitize the ‘dark matter’ of offline conversations comprising field sales engagements, which has broad extensibility across verticals and depth in downstream actions that can be instrumented from this data, such as customer and product insights,” he told TechCrunch via email.



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