MarTalks: Cracking the Code for those first deals: Enterprise Sales for Startups

Episode notes

In the latest *MarTalks* episode, I had the privilege of hosting three enterprise sales powerhouses—Brad Habansky, Chris Sterbenc, and Brian McGlynn—to discuss one of the most daunting challenges for startups: landing that first big deal. These seasoned pros shared their war stories, scars, and hard-earned wisdom on navigating the complexities of enterprise software sales. Here’s what stood out: --- ### ** Selling Innovation is Hard Work** Brad Habansky recounted his early days at CommerceTools, introducing "composable commerce" to a U.S. market that had no idea what it was. Before he could even pitch flexibility or scalability, he had to convince prospects why they should trust the cloud—a revolutionary concept at the time. His journey was a masterclass in persistence, education, and rapid iteration. --- ### ** Iteration is Key** Chris Sterbenc shared how selling for startups often requires constant refinement of your pitch. Early on, parts of his presentations fell flat (I hate it when that happens) —but by analyzing what resonated with prospects, he adapted quickly.