Let's Chat

Ankesh Kumar had already sold multiple companies for substantial exits—AT Systems ($22M), Personic ($25M to Kronos and Google). But in 2019, he spotted a gap in the outbound sales market. While competitors like Intercom and Drift dominated inbound website chat, no one was solving the outbound problem: salespeople sending cold emails with no way to engage prospects in real-time conversation. Kumar mocked up an idea in May 2019, entered Salesforce's demo jam, and won. That validation was enough. By the time of this interview (late 2019), he had built the entire infrastructure, integrated with Salesforce, Sales Loft, and Outreach, and was preparing for launch.

With just one developer and himself, operating on a lean $5,000/month burn rate, Kumar shipped a fully functional chatbot builder in four months. The product was elegant in its simplicity: when a salesperson sends a cold email, they can include a chatbot link that lets the prospect explore case studies, videos, and personalized content without leaving their inbox. The real power, Kumar believed, was in the data: as prospects engage with different content pieces, salespeople learn what actually interests them and can personalize follow-ups accordingly.

Rather than waiting for customers to find him, Kumar used his own product as a go-to-market machine. He identified his ideal customer: demand generation directors at 50-1,000 person SaaS companies. Every morning, he sent 30 personalized outbound emails using Lusha and LinkedIn for contact data, embedding his chatbot so prospects could see the product in action. The results were exceptional: 50% open rate (versus a 5-10% industry average) and 10% engagement rate (versus 1-2% typical). He was essentially demoing the product while prospecting, letting prospects feel the value firsthand rather than pitching them on features.

The cold email approach worked remarkably well, but Kumar deliberately avoided charging customers immediately. Instead, he focused on getting design partners and validating the core thesis: does embedding chat in outbound emails actually increase engagement and conversion? He had a few early accounts running A/B tests, sending 1,000 emails with the chatbot and 1,000 without, to prove the lift before scaling. His philosophy was investor-grade: understand CAC, LTV, and competitive differentiation at low burn before raising capital or spending aggressively.

The trickier challenge was partnership distribution. Kumar was pitching Sales Loft, Outreach, and email signature companies like Signaturely as potential integrations. He had to convince them that letting a scrappy two-person startup embed chatbots into their platforms was worth it. His pitch: nimbleness and AI/ML capability to iterate features in 24 hours, something larger teams couldn't match.

By the end of 2019, Let's Chat was pre-revenue but generating real traction. Kumar aimed to have five paying customers by December 2019, though he viewed the metric loosely—a partner relationship with a flagship account was as valuable as a paying customer at this stage. His five-year vision was audacious: one million salespeople paying $25/month, equaling $250 million in monthly revenue. For now, he was keeping burn low, shipping fast, and proving the market would pay for better ways to engage prospects in outbound sales.