Ershad Kunnakkadan, who was appointed as the new CEO of Gumroad on Thursday, began his journey in Kerala’s free-software circles long before he entered the leadership corridors of San Francisco’s tech world.
At 33, the engineer who once learned coding through local open-source communities now heads the e-commerce platform that records over $100 million in Gross Merchandise Value (GMV). Founder Sahil Lavingia announced the transition on X, calling Ershad “the perfect leader” to succeed him after 14 years at the helm.
Ershad, who moved to New York only in May this year as Gumroad’s staff software engineer after working remotely with the company since 2020, responded with characteristic modesty, saying he was “honoured” and “ready to serve our creators even more.” The news has sparked pride across Kerala, where his earliest steps in computing were shaped in a government school classroom, through a gifted Ubuntu 8.04 CD, and with the support of Swathanthra Malayalam Computing (SMC) — a free software collective engaged in development, standardisation, localisation, and popularisation of various free and open software in the Malayalam language.
His rise was detailed in a widely shared post by Menlo Ventures partner Deedy Das, who called it an “incredibly inspirational story.” Das describes a teenager obsessed with terminals, scripting contests, Linux administration, security, and blogging — interests that eventually overshadowed college life. Ershad dropped out of a little-known private engineering college in Kerala after his second year, assuring his family he would “earn a degree somehow,” which he later did through a distance programme while gaining real-world experience: internships, free-software workshops, finding security bugs in Github and Prezi, and securing a Google Summer of Code selection.
Even while working for companies such as BigBinary from Kochi, he stayed connected to Kerala’s open-source meetups and Malayalam computing initiatives. Das contrasts his journey with the classic Silicon Valley trajectory: no pedigree, no MBA, no loud personal branding — just a quiet, dense body of work.
Ershad entered Gumroad as a consultant, grew into a senior engineer, moved to Abu Dhabi after marriage, and finally to New York on an O-1 visa. Inside the company, he became the engineer trusted with the “boring, crucial stuff”: scalability, security, payouts, and infrastructure that kept millions of users and over a billion dollars in creator earnings running smoothly.
So when Gumroad’s board began looking for a new CEO, Das writes, “it was clear who was the best fit.” For Kerala’s tech community, Ershad’s ascent is a reminder that global leadership can emerge from open-source roots, quiet persistence, and the discipline of showing up — every day.
