Early in his career, Dermody was the Director of Research and Development at KnoahSoft. He was the Co-Founder of Symbiont.io, which he later resigned from for health-related reasons. In 2013, he was the co-founder and Lead Developer of Counterparty which utilized the Bitcoin blockchain for earl versions of smart contracts. In addition, he was the Co-Founder of CtiPath which specializes in bespoke monitoring and managed services for enterprise application stacks. Since December 2017, Dermody has been the Principal of Stoic Capital, an asset management company that focuses on cryptocurrencies.