Because it was an intimate environment, you had a lot of people launching ventures, and it showed me that if you had an idea and you wanted to get something done, you could do it.

BY ALINA DIZIK

Contacting customer service feels like a chore to most consumers. But Chatdesk cofounder Andrew Olaleye T’13 says the exchange doesn’t need to feel dreadful. At Chatdesk, consumers chatting with a rep often crack a smile—or make a purchase—after the exchange.

Olaleye describes Chatdesk as “Uber for customer support.” With roughly 115 employees and 8,000 experts, the New York-based company expands the traditional notion of customer service, by creating a network of freelance workers they call brand experts that help companies respond to support inquiries across social media, email, and chat.

Chatdesk recruits U.S.-based brand experts to provide responses to customer questions directly on social, which drives sales. Often responses use emojis or slang per the individual company’s guidelines to be more relatable. We help find people who understand your brand and give them the technology to speak with you in your voice and increase your sales, he says.

The combination of digital customer service agents and a machine-learning platform allows companies including Unilever, Olaplex, and Barkbox to scale their customer support teams and drive sales through higher social media engagement, he says. The company now supports more than 70 beauty brands, a category that’s known for its social media users. We’re turning customer support into a sales engine, says Olaleye, who launched the company in 2016.

For Olaleye, launching the digital customer service platform meant leaning on his entrepreneurship training at Tuck. When coming to business school the former finance professional was looking to work in an area that allowed for “personal impact,” he says. After two years, many of the courses and people he met had reinforced his interest eventually launching his own entrepreneurial venture. Because it was an intimate environment, you had a lot of people launching ventures, and it showed me that if you had an idea and you wanted to get something done, you could do it, says Olaleye.

After graduating, Olaleye landed a job at McKinsey & Co. and worked as a consultant primarily in Sub-Saharan Africa. During that time he met his cofounder Aneto Okonkwo and the two later began Chatdesk. It helped me learn about the challenges in how companies are trying to digitize and use technology, says Olaleye, who is also of Nigerian heritage.

Today, the company has grown to support more than 700 brands across the U.S., Europe, and Australia. Olaleye continues to participate in Tuck’s active entrepreneurship scene including mentoring students and attending alumni events. I love how Tuck has transformed into a hub that’s embracing entrepreneurs, he says. More people are now leaving Tuck and going straight to their own companies and small startups.

This story originally appeared in print in the winter 2023 issue of Tuck Today magazine. Read the full article “Meet the Next Generation of Tuck Founders.”