“Being successful, whether it's in Cambodia or Laos or Kenya, is a process of a shared negotiation of meaning.”

Sameer Raina spent 20 years in business process outsourcing before joining Digital Divide Data eight and a half years ago, initially as a consultant and later as CEO. He'd grown up in India, worked across Asia, done a couple of successful startups, and was experiencing career burnout in his early 40s when he started looking for something more interesting than chasing financial goals. DDD offered a chance to build a scalable, profitable business while creating social impact, a formula he believes more organizations should try. Under his leadership, DDD transformed from a digitization operation into an AI-first company, a three-year journey that positioned associates to build skills for the future of work. The shift made sense commercially and developmentally: if learning Microsoft Office was essential 20 years ago, then understanding ChatGPT, labeling, and annotation for dataset creation will be essential in five to ten years. "For us, growth needs to be inclusive, it needs to be sustainable, and it needs to be profitable," he says, emphasizing that inclusivity comes first.

The biggest challenge hasn't been the technology itself but people's resistance to change, especially among senior management. Building an AI-first culture means making these tools as routine as any other workplace software, a process Raina estimates will take three to five years. He's also navigating the classic social enterprise tension between commercial outcomes and social mission, relying on a board that balances both perspectives. Looking ahead, he's exploring nation capacity building partnerships with governments in Cambodia and Laos, where officials are surprised by the sophistication of DDD's AI work. The pace of technological change has caught everyone off guard, but Raina's focus remains on broadening the tent to be more inclusive and creating multiplier effects beyond DDD's own associates. His favorite success stories are the random texts he gets from alumni years later, thanking him for training that helped them land better jobs and higher salaries.