Jennifer Olsen has had a lengthy career in marketing, working for both start-ups and established brands. She is currently the CMO of UNTUCKit, a clothing company that has reached $200 million in sales.Previous to this role, she spent 10 years in marketing at Gap. She also held the role of CMO at Crate and Barrel and Stitch Fix, along with becoming Vice President of Marketing at Yahoo.In this episode, Jennifer talks about her career path, side hustles and how her single dad inspired her work ethic. This is a great discussion with a marketer who has worked in both start-ups and the major brand corporate playing field. She also discusses her thoughts on marketing in the digital space to spread brand messages.