While AI note-takers are becoming common in video meetings, Siro is taking that same idea offline, to field sales teams talking to customers face-to-face. On Wednesday, the company announced a $50 million Series B round led by SignalFire, with participation from 01 Advisors (run by former Twitter execs Dick Costolo and Adam Bain) and other notable investors from Square, Yelp, Snap, and Squire.
This new round brings Siro’s total funding to $75 million, all focused on building an AI-powered platform that supports salespeople on the ground, not just in the boardroom.
Siro’s founder, Jake Cronin, got the idea during a college summer job. While his peers were working amusement park shifts, he opted to sell kitchen knives door-to-door—and did well. The next year, he managed a team of junior sellers, but struggled to coach them in real time. That pain point stayed with him and became the foundation for Siro.
After a stint at McKinsey, Cronin began building Siro himself, coding the product from scratch. “So much of sales is manual,” he said. “The best way to help field reps is not through CRM dashboards, but by coaching them where it matters—in real conversations.”
Digitizing the ‘Dark Matter’ of Field Sales Conversations
Siro’s AI sales coaching platform records and analyzes in-person meetings via a mobile app. Reps can review transcripts, submit top calls to a shared dashboard, and sort them by peer engagement. It’s a way to surface best practices across teams and help new reps learn directly from real-world interactions.
The company also tailors its AI to specific industries. For example, it trains models to provide sales coaching for HVAC reps, offering insight into how reps handle objections and build trust with clients. A general-purpose model helps evaluate rapport and conversation quality in any sales setting.
Investors are backing the vertical focus. Wayne Hu of SignalFire said the firm looks for startups that create proprietary data advantages. “Siro is unlocking the dark matter of offline sales conversations,” he explained. “That opens up deep insights—from customer sentiment to product feedback—and drives better actions across sales organizations.”
With fresh capital, Siro plans to expand into more industries and continue training models that make field reps smarter, faster, and better supported—no matter where they’re selling.
