His association with The Onion began when he published his first article on the site at age 17 as a high school student in Madison, Wisconsin.[6] He also published a satirical newspaper on campus and sent articles to The Onion, eventually attracting the latter's attention.[7] Later, he began to work at the office of the publication and landed an internship during his senior year in high school as the site's first intern.[8] At Columbia, he also freelanced for the publication, publishing a total of 25 articles for which he received a payment of $20.[6][5] He was hired out of college and became manager editor of the website at age 24.[6][9] At The Onion, Koechley was responsible for creating the Onion News Network and gravitated towards tech content.[10]
Koechley joined MoveOn in 2009 to produce viral media content for the nonprofit group.[11] There he met Eli Pariser and the two began to develop a concept for a platform that generates viral content devoted to significant social issues, what they call "social media with a mission".[8] Their business plan appealed to Chris Hughes, who provided them with $500,000 in seed capital.[12] They also attracted seed capital from BuzzFeed co-founder John Seward Johnson III and Reddit co-founder Alexis Ohanian.[13]
In 2012, Koechley and Pariser launched Upworthy.[12] By the end of October 2012, it has attracted 8.7 million users, leading Business Insider to name it the fastest growing media company in the world.[13][14]
In 2015, he apologized for Upworthy's out-sized success and pledged to change the algorithm, saying:"We sort of unleashed a monster. Sorry for that. Sorry we kind of broke the internet last year. I'm excited going forward to say goodbye to clickbait."[15][16]
In 2017, Koechley announced his departure from Upworthy.[17] He has been working with Compass, Inc. founder Robert Reffkin, in writing the book No One Succeeds Alone: Learn Everything You Can from Everyone You Can, published in 2021.[18]
In 2021, Koechley joined The Our City PAC, a progressive political action committee supporting left-leaning mayoral and New York City Council candidates.[19][20]