Darren writes about the operational mess of scaling a company, specifically what breaks in operations and IT inside small to medium-sized businesses, and why vendor sprawl is usually a symptom of something bigger. He is co-founder and COO of Ensurva. Before Ensurva, Darren co-founded Assembly Payments, now MX51 and Zai, which scaled to over $28B in transaction volume and raised over $100M in venture capital. As COO of Hapana, he grew headcount from 56 to 120+ across five countries and co-led a $17M funding round. Both experiences involved the same quiet pattern: vendor relationships multiplying faster than anyone could track them, and the operational cost of that showing up months or years later. His work combines strategy, operations, commercial strategy, capital raising, marketing, HR, project management, and tactical execution. He has sat in the seat where tools get bought without anyone telling IT, where departments end up paying different vendors for the same capability, and where the real cost of a surprise renewal is not the invoice but the scramble around it. On the Ensurva blog, he writes for operations leaders mapping vendor ecosystems they did not design, and for IT leaders who want to stop discovering vendor relationships by accident. He draws on what he has seen firsthand across the companies he has built and scaled.
