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Siro Raises $50M to Revolutionize Sales Coaching with AI

May 21, 2025
Siro Raises $50M to Revolutionize Sales Coaching with AI

Siro Secures $50 Million to Enhance AI-Powered Sales Coaching

The presence of AI note-takers in meetings is becoming increasingly common, offering transcription and action item summaries. Siro aims to replicate this benefit for sales teams conducting in-person customer interactions.

On Wednesday, the company announced the successful completion of a $50 million Series B funding round. This round was spearheaded by SignalFire, with notable participation from 01 Advisors, the venture capital firm founded by Dick Costolo and Adam Bain.

Investment Details and Total Funding

Additional investors included Square CPO Saumil Mehta, the founders of Squire – Songe LaRon and Dave Salvant – Michael Stoppelman, former Yelp SVP of Engineering, and Ding Zhou, formerly VP of Engineering at Snap.

To date, Siro has accumulated a total of $75 million in funding.

The Genesis of Siro

Founder Jake Cronin’s inspiration for Siro stemmed from a personal experience during his college years. He faced a choice between working at an amusement park or engaging in door-to-door sales of kitchen knives.

Opting for the latter, he achieved significant earnings. Subsequently, he established an office to recruit and manage other sales representatives. However, he quickly recognized the challenge of providing consistent coaching to all junior team members while not being physically present.

siro lands $50m to expand its ai-powered coaching for sales repsFollowing his time at McKinsey, Cronin began developing Siro, personally coding the initial core functionalities.

“My experience running the knife sales operation highlighted the substantial amount of manual effort involved in sales,” Cronin explained in an interview with TechCrunch. “Further research led me to believe the greatest opportunity lies not in data enrichment or CRM, but in directly improving the performance of sales representatives in the field.”

How Siro Works

Siro utilizes an application to transcribe sales conversations. A key feature is a company-wide dashboard.

This dashboard allows sales personnel to submit recordings of successful calls, categorized by peer engagement. Other representatives can then review these top-performing calls to gain insights and enhance their own on-site sales techniques.

siro lands $50m to expand its ai-powered coaching for sales repsCronin stated that Siro develops specialized models tailored to specific industry sectors, such as HVAC sales coaching. The company also employs a general model to assess a salesperson’s rapport-building skills and their ability to navigate objections.

SignalFire’s Perspective

Wayne Hu, a partner at SignalFire, emphasized the firm’s focus on investing in companies with a distinct data advantage within specific market segments.

“Siro’s solution effectively digitizes the previously undocumented realm of offline conversations that characterize field sales engagements,” Hu communicated to TechCrunch via email. “This offers extensive applicability across various industries and enables the implementation of actionable insights derived from this data, including customer and product intelligence.”

#AI sales coaching#sales enablement#Siro#funding#venture capital#sales performance