Wingman Revolutionizes Sales Coaching with Real-Time Conversational AI
In most sales organizations, managers only have visibility into about 5% of what actually happens on customer calls. The remaining 95%—the crucial objections, competitor mentions, and subtle buying signals—stays locked inside the rep's head or lost in incomplete notes. Shruti Kapoor, Co-founder of Wingman (now acquired by Clari), is changing that. By building a "Wingman" that listens to live sales calls and provides real-time coaching "cards," Shruti is turning the dark art of sales into a data-driven science.
Shruti Kapoor’s journey is one of high-pedigree execution. An alumna of IIM Ahmedabad with experience at Morgan Stanley and Payoneer, Shruti saw firsthand the gap between what CRMs recorded and what customers actually said. Alongside her co-founders Muralidharan Venkatasubramanian and Srikar Yekollu, she took Wingman through the prestigious Y Combinator (W19 batch) and eventually led it to a successful acquisition by revenue operations giant Clari in 2022.
The 95% Data Gap
Sales managers often coach based on the "outcome" (the deal won or lost) rather than the "process" (the actual conversation). Shruti realized that 95% of call information is lost because reps can't listen, talk, and take detailed notes simultaneously. Wingman captures that missing 95%, providing a "game tape" for sales coaching.
The Problem: The Invisibility of the Sales Floor
Traditional sales coaching is reactive. A manager sits down with a rep once a week to review a deal, but by then, the actual conversation is days old. The rep’s memory is biased, the CRM notes are sparse, and the opportunity to correct a mistake has passed. For a scaling startup, this lack of visibility is a major roadblock to repeatable revenue.
"I was leading a sales team and I felt blind," Shruti explains. "I could see the number of calls being made, but I had no idea why some reps were closing and others weren't. We were losing massive amounts of information that could have helped us win."
The Solution: A Real-Time "Wingman" for Sales Reps
Wingman is a conversational intelligence platform that integrates directly with tools like Zoom, Google Meet, and Slack. It records, transcribes, and analyzes calls in real-time, but its true power lies in its ability to intervene *during* the call.
The Wingman Workflow
- Automated Integration: Wingman joins scheduled calls automatically, recording and transcribing in high fidelity.
- Real-Time Battlecards: If a customer mentions a competitor, a "card" pops up on the rep's screen with the exact talk track to use.
- Note-Taking Automation: Reps can focus on the customer while the AI flags key moments, objections, and follow-up items.
- Coaching Library: Managers can quickly review the "highlights" of 100 calls in the time it used to take to listen to one, creating a library of "Golden Calls."
Building an MVP: From Audio Player to AI Coach
Wingman didn't start with complex AI. The first version of the product—their Minimum Viable Product (MVP)—was simply a tool that made it easy to record and play back audio from sales calls. Shruti and her team manually reviewed calls to find the "magic moments" before they ever wrote a line of automation code.
"We started with people who were desperate to solve the problem," Shruti recalls. "Our first customers were managers who were willing to listen to recordings just to understand what was going wrong. We only built the AI once we understood exactly what data points were most valuable for them."
Wingman Scale & Milestones
- Y Combinator W19: Part of the world's most prestigious startup accelerator.
- Clari Acquisition: Successfully acquired by the leading Revenue Operations platform in 2022.
- Real-Time Intervention: One of the few platforms that provides coaching *during* the call, not just after.
- Global Reach: Serving thousands of sales reps across the US, India, and Singapore.
The Pivot: Beyond Simple Recording
Initially, Wingman was seen as a "recording tool." However, Shruti realized that recording alone didn't solve the performance problem—it just created more data for managers to ignore. The team pivoted to focus on Real-Time Conversational Intelligence.
By moving from "post-call analysis" to "live-call assistance," Wingman became an essential tool for the rep, not just a monitoring tool for the manager. This shift was critical for their Product-Market Fit, as it aligned the interests of both the individual contributor and the leadership team.
Founder's Lesson: The Customer "No"
Shruti believes a "No" from a customer is better than a "Maybe." "You want to get to a definitive answer as quickly as possible. A 'No' allows you to stop wasting resources and move to the next opportunity. A 'Maybe' is what kills startups."
The Meaning of Entrepreneurship
For Shruti, entrepreneurship is about obsession with the problem. She defines a founder as someone who cannot stop thinking about a specific inefficiency until they have built a way to fix it. She also highlights the importance of resilience—the ability to face the "99 nos" to find the "1 yes" that changes the company's trajectory.
"Entrepreneurship is a solo journey in many ways," she reflects. "You have to hold your self-esteem high even when everyone tells you it won't work. The best entrepreneurs are those who are ready to be wrong and pivot until they are right."
Lessons for Aspiring SaaS Founders
1. Sell Before You Build
Shruti recommends talking to at least 50-100 potential customers before writing significant code. Understanding the "pain" is more important than building the "feature."
2. Retention is the Only North Star
Don't just look at new sales. Look at how many customers are still using the product six months later. If they aren't sticking, you haven't solved the core problem yet.
3. Focus on the Rep's Experience
In B2B SaaS, the person paying for the tool (the manager) is often not the person using it (the rep). If the rep hates the tool, the manager will eventually stop paying for it. Build for the end-user first.
Wingman is proving that the future of sales is collaborative. By providing a digital coach for every call, Shruti Kapoor and her team have turned the sales conversation into a transparent, improvable, and winning process.
Founder's Perspective: The Power of 'Maybe'
Don't fall for the trap of the polite 'Maybe.' In sales and in fundraising, a polite 'no' is a gift. It gives you your time back. The 'maybe' is a thief that steals your focus.
About the Guest
Shruti Kapoor is the Co-founder and former CEO of Wingman. An alumna of IIM Ahmedabad, she has a background in investment banking and sales leadership at Payoneer. Under her leadership, Wingman grew into a leading conversational intelligence platform, was selected for Y Combinator, and was ultimately acquired by Clari. She currently serves as the Head of International Business at Clari, driving the expansion of conversational AI across the global revenue ecosystem.
Wingman (by Clari) is a conversational intelligence platform that helps sales teams win more deals. By providing real-time coaching, automated call transcription, and actionable deal insights, Wingman helps companies improve sales performance and close the visibility gap in their revenue operations.