Winn has written for periodicals such as Washington Post, Christian Century, Soul Journey, Christianity Today, In Touch, Campus Life, Leadership Journal, Radiant, Preaching Today and Clear & Seven. For six years, Winn was the Deeper Walk editor for Relevant Magazine. His first solo book, Restless Faith: Hanging on to a God Just out of Reach is a candid exploration into the perplexing, riveting and mysterious nature of God - and the humility we discover in the encounter. His second book Let God: The Transforming Wisdom of Francois Fenelon enters conversation with a 17th century French spiritual guide. Winn's most recent book, Holy Curiosity: Encountering Jesus' Provocative Questions, explores the strange reality that Jesus often held out a question rather than an answer. Winn's first fiction was the epistolary novel Love Big, Be Well: Letters to a Small-Town Church which narrates the story of Jonas McAnn and the community of Granby Presbyterian via letters Jonas writes to his friends (i.e. "congregation). Winn's most recent book is A Burning in My Bones, the authorized biography of Eugene Peterson.

A pastor for 25 years and the founding pastor of All Souls in Charlottesville, Virginia, Winn and his family now live in Holland, Michigan, where he teaches at Western Theological Seminary and directs the Eugene Peterson Center for Christian Imagination. Winn earned a PhD in religion and literature from the University of Virginia.