Checkler most recently served as vice president of communications for XPO, Inc., where he led the corporate and investor communications organization from 2018 to 2022. Prior to XPO, he was a media relations executive with Peppercomm, Inc. from 2015 to 2018. He began his career with an 11-year tenure as a reporter for Dow Jones & Company, where he covered business and financial news for The Wall Street Journal.