AI tools are everywhere in virtual meetings — taking notes, suggesting follow-ups, and summarizing action items. But what about sales reps who meet customers face-to-face? Siro wants to bring the same smart support to the field.
The startup just raised $50 million in Series B funding to expand its AI-powered sales coaching platform. The round was led by SignalFire with participation from 01 Advisors, the VC firm run by former Twitter execs Dick Costolo and Adam Bain. Other investors included Square CPO Saumil Mehta, Squire co-founders Songe LaRon and Dave Salvant, and former engineering leaders from Yelp and Snap.
This brings Siro’s total funding to $75 million.
Siro was born from a simple idea. During college, founder Jake Cronin sold kitchen knives door to door. It paid well, so the next summer, he opened an office to manage his own team of reps. But he quickly realized that coaching every rep in real time was impossible. That pain point stuck with him.
After working at McKinsey, Cronin decided to build the solution himself. He started coding Siro from scratch.
“I noticed how much of sales work is still manual,” Cronin said. “Good software could make a real difference, especially for reps out in the field.”
Siro helps by recording and transcribing in-person sales meetings. The app makes it easy for reps to share top-performing calls and review peer feedback. It’s a way to crowdsource coaching and learning — straight from the frontline.
The company also trains AI models tailored to specific industries. One version is built for HVAC field sales. Another measures soft skills like rapport and rejection handling using a general-purpose AI engine.
Wayne Hu, a partner at SignalFire, said the firm was drawn to how Siro captures offline conversations — the so-called “dark matter” of sales. Turning that into data creates value not just for coaching, but for product insights and customer understanding.
As more sales reps spend their time on the go, tools like Siro are helping teams level up — without slowing them down.
