Siro Secures $50M Series B for AI Sales Coaching Expansion
Siro, an AI-powered sales coaching platform, announced a $50 million Series B funding round led by SignalFire. The round includes participation from Dick Costolo and Adam Bain’s VC firm 01 Advisors, along with other notable investors like Square CPO Saumil Mehta.
This latest funding brings Siro's total raised to $75 million. The company plans to use the investment to further develop its platform and expand its reach within various sales verticals.
From Kitchen Knives to AI Coaching
Founder Jake Cronin's experience selling kitchen knives door-to-door inspired Siro. He recognized the challenges of coaching junior sales reps effectively. This led him to develop Siro, initially coding the core product himself after a stint at McKinsey.
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. The biggest opportunity is improving the lives of sales reps on the ground.
How Siro Works
Siro's app transcribes sales meetings and offers a company-wide dashboard. Sales reps can share successful calls, sorted by peer engagement. This allows other reps to learn from top performers and gain insights for improving their own sales visits.
The platform leverages industry-specific AI models, such as for HVAC sales coaching. It also uses a general-purpose model to analyze rapport-building and rejection handling.


Investor Perspective
Wayne Hu, a partner at SignalFire, highlighted Siro's focus on digitizing offline sales conversations. He emphasized the potential for broad applicability across various industries and the valuable customer and product insights that can be derived from this data.
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.