
Shruti Kapoor, Wingman (acquired by Clari)
40 Failed Sales Meetings to 90% Inbound Revenue
Shruti Kapoor was running a sales team at Payoneer in India when she realized sales managers had no visibility into why some reps consistently outperformed others. Call recordings existed, but no one had figured out how to turn that data into actionable coaching. So Shruti and two co-founders - both former Google engineers - built Wingman, a platform that analyzes sales conversations and delivers real-time coaching feedback. They built an MVP in five months and landed their first paying customer by October 2018. But scaling beyond their personal network proved brutal. A sales consultant booked 40 meetings with their ideal customers, and Wingman closed zero of them. The problem was not the product. It was the perceived effort customers saw in adopting a new tool that required them to create content on a new platform before seeing any value. The fix was repositioning. Instead of selling the full platform, Shruti identified features that required zero setup - like real-time monologue alerts and call bookmarking - and led with those. She also created templates so customers only had to fill in blanks instead of starting from scratch. That shift moved Wingman from near-zero revenue to six figures in about three months. From there, Shruti went all in on inbound marketing. She realized salespeople are social buyers who rely on peer recommendations, so she focused on community-driven word of mouth. Wingman's own customers started posting about the product in Slack communities, Reddit threads, and sales leader forums - organically at first, then with gentle nudges from the team. That community engine, combined with SEO, social media content, and personal branding, drove over 90% of Wingman's revenue. The company grew to mid-seven figures in ARR, 300+ customers, and about 60 employees - all on a $2.3 million seed round from Y Combinator. In 2022, Clari acquired Wingman at a 15-20x revenue multiple.






















