Quest Alliance began its organisational journey as digital technology was about to unfold sweeping changes in India, including in the areas of education and employment. As if to symbolise its tryst with technology, it is nestled in India’s “silicon valley” city of Bengaluru. Today, it also happens to enjoy the patronage of an enviable list of marquee donors ranging from leaders in the financial services industry and information technology to multilateral development agencies and Indian Government. Over the course of its work with these partners, Quest Alliance 1 has come to serve as an interesting node in the arena of skill development and operates at the intersection of education, technology and youth employment. Established in 2005, it started as an earnest but modest enterprise. From 2009—when it had seven people and a sudden crisis of funding at hand—till 2022, it saw rapid acceleration. By the end of 2022, it had a team of 234 handling over INR 62 crore worth of annual funding. What Quest was working on—“Enabling self-learning”—was highly topical and certainly aided its growth, but amidst this growth something unusually remained steadfast: the extent of its investment on learning, development and capacity building of its own team. This holds significance for civil society where sourcing and building talent is a continuous pre-occupation for leadership. The case engages with the journey of Quest and its founder Aakash Sethi, and explores what it takes to put in place the internal scaffolding to hold together this deliberate and sustained focus on self-learning and development of its own people. It also engages with Quest’s work towards evolving a model of talent-building of young people in schools as well as those in transition from education to employment: anchored in the notion of young people as self-learners equipped with 21st century skills. The latter part of the case explores how Quest has crafted its own people management practice around the “self-learner” and gives learners the opportunity to reflect on the challenges of building and maintaining a way of being, doing and relating in a rapidly growing organisation.