Siro Secures $50 Million to Expand AI-Driven Sales Coaching As businesses increasingly rely on AI to capture and analyze meeting data, Siro is pushing the frontier by applying similar technology to in-person sales interactions. On Wednesday, the company announced it has secured $50 million in a Series B funding round led by SignalFire, with significant contributions from 01 Advisors, founded by Dick Costolo and Adam Bain. Other investors include Square's Chief Product Officer, Saumil Mehta; the founders of business management software Squire, Songe LaRon and Dave Salvant; former Yelp Senior Vice President of Engineering, Michael Stoppelman; and former Snap Engineering Vice President, Ding Zhou. With this investment, Siro's total fundraising to date reaches $75 million. Jake Cronin, the founder of Siro, drew inspiration from his early experiences in sales. During college, he chose to sell kitchen knives door-to-door over working at an amusement park. This decision proved lucrative, and the following year, he expanded his efforts by opening a sales office to train and manage a team of junior reps. However, Cronin soon realized that he couldn't physically oversee and coach every sales representative. After gaining valuable experience at McKinsey, he decided to leverage technology to address this challenge, starting by coding the initial version of Siro himself. "The biggest opportunity in sales, I found, isn't just in data enrichment or customer relationship management," Cronin explained in an interview with TechCrunch. "It's in enhancing the daily activities of sales representatives on the ground." Siro's platform transcribes and analyzes face-to-face sales meetings through a mobile app. Key features include a company-wide dashboard where sales reps can share successful calls and receive peer feedback. This collaborative environment allows reps to learn from their colleagues' best practices and gain insights into improving their own performance during on-site visits. Moreover, Siro's AI models are tailored to specific industries, such as heating, ventilation, and air conditioning (HVAC) sales, providing targeted coaching and feedback. The platform also employs a general-purpose model to evaluate interpersonal skills, including rapport building and handling rejections, ensuring comprehensive support for sales professionals. Wayne Hu, a partner at SignalFire, emphasized the unique value Siro brings to the table. "We look for companies that have a robust data advantage in specific sectors," Hu stated via email. "Siro's solution helps digitize the often overlooked 'dark matter' of offline sales conversations, offering broad applicability across various industries and deep insights into downstream actions, such as customer and product feedback." With this fresh injection of capital, Siro aims to further refine its technology and scale its operations, ultimately empowering sales teams to perform better and more consistently. The company's innovative approach to sales coaching is poised to transform the way businesses support their frontline employees, bridging the gap between real-world interactions and data-driven insights.