Barry cited Mailchimp as the primary long-term competitive reference point. He estimated, based on trends from previously reported figures, that Mailchimp generates approximately $750 million in annual revenue, possibly approaching $1 billion, after nineteen years in business. This is Barry's estimate of a competitor and is not a Mailchimp-confirmed figure.
Barry told Latka he met Mailchimp CEO Ben Chestnut at the Inc. 5000 conference in 2018, where Chestnut spent thirty minutes discussing how Mailchimp's free plan drove significant enterprise account acquisition. Barry also referenced Constant Contact as a competitor that Mailchimp displaced through its freemium strategy. He described ConvertKit's growth curve as ahead of where Mailchimp was at the equivalent eight-year mark in its history, though he acknowledged he does not have Mailchimp's exact historical figures.