Sears was born in New York, and grew up in the East Coast of the United States. He graduated from Yale University and the Iowa Writers' Workshop. He won the 1999 Peregrine Smith Poetry Competition and the 2000 Western States Poetry Prize for his book of poems, The Brink. His first book-length collection, Tour, was published in 1987. He has also published four chapbooks of poetry and two teaching books, Secret Writing and Gonna Bake Me a Rainbow Poem. His work has been published in many magazines and literary journals, widely anthologized and included in the radio series, The Writer's Almanac. His most recent full-length book is titled Green Diver.

Sears founded and manages the Oregon Literary Coalition and co-founded the non-profit organization Friends of William Stafford. He formerly taught creative writing at Reed College and has since taught for the Northwest Writing Institute at Lewis & Clark College. He is active in the publishing company Rubberstampmadness Inc. in Corvallis and Community of Writers in Portland.