Siro, a startup focused on using artificial intelligence to assist sales representatives working face-to-face with customers, has raised $50 million in a Series B funding round led by SignalFire. Notable participants included 01 Advisors—the venture firm founded by former Twitter executives Dick Costolo and Adam Bain—Square’s Chief Product Officer Saumil Mehta, Squint founders Songe LaRon and Dave Salvant, and tech veterans Michael Stoppelman and Ding Zhou. With this latest investment, the company’s total funding now amounts to $75 million.
Founder Jake Cronin conceived the idea for Siro during his college years, rooted in experiences selling kitchen knives door-to-door. Cronin initially took on sales work himself, and after achieving notable success, he launched his own office and recruited agents. However, he quickly recognized the limitations of coaching new hires effectively while being off-site. Recounting this experience, Cronin remarked that most existing sales tools focused on data management and customer relationships, missing the significant opportunity to improve the daily experiences of field sales representatives directly.
Siro’s technology meets that need by recording and transcribing face-to-face conversations via a dedicated mobile application. It also provides a centralized dashboard where successful interactions can be shared across the sales team. Representatives can browse through the most effective sessions and gain insights into best practices, such as building rapport and managing rejection.
Cronin stated that Siro employs customized AI models tailored to specific industries—for example, sales practices in HVAC—and also utilizes broader models capable of gauging the quality of interpersonal interactions. According to SignalFire partner Wayne Hu, the firm was particularly drawn to Siro’s ability to extract valuable insights from offline interactions. Hu praised the startup for illuminating what he referred to as the “dark matter” of sales conversations, emphasizing the substantial potential for generating actionable insights in product and customer management as well as improving sales efficiency across diverse industries.
