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Douglas Lail has worked in a variety of roles since 2001. Douglas began as an Adjunct Instructor at Guilford Technical Community College in 2001. In 2005, they worked as a Senior Art Director at Genre Brand Communication, and as an Abstract Artist at MOTIVE ~ Abstract Artist/Painter Douglas Lail. Douglas then worked as a Creative Services Manager at THOMASVILLE FURNITURE and DREXEL HERITAGE from 2006 to 2009. In 2014, they founded The "HELLO MY NAME IS..." Project and began volunteering with the Art Therapy Program at ABCCM. In 2017, they worked as a Creative Services Manager at Magnussen Home Furnishings. Since 2019, they have been working as a Portrait Artist at Douglas Lail - Fine Art Portraiture, and since 2020 they have been working as a Marketing Director and Creative Strategist at THS Creative.

Douglas Lail's education history includes attending Asheville Academy of Art in 2014 to study Traditional Oil Painting, Academy of Art University from 2012 to 2013 to study Painting, Guilford Technical Community College from 1998 to 1999 to obtain an Associate of Arts and Sciences (AAS) in Design and Visual Communications, and Asheville-Buncombe Technical Community College from 1993 to 1995 to obtain an Associate of Arts and Sciences (AAS) in Medical Laboratory Technology.