A short YouTube monologue by Jason M. Lemkin arguing that sales reps who have experience selling in difficult environments (complex products or tougher buyer contexts) perform better and adapt when moving to new roles. He contrasts reps who sold easy, familiar tools—who often struggle—with those proven in harder selling conditions, recommending hiring the latter.
It's always hard and all startups are hard but was it a little bit harder? Even harder because they just fly when they come into an environment that's easier. See this at all stack from the most junior sales rep all the way to the top but when they come into environments that are a little bit harder to sell in they melt. I often see folks that have sold traditional sales tools, traditional sales buyers number one is when they come into a product that's more complicated to sell or in a CRM they're in gong. They're in all these products all the time and so selling them it's not selling that's easy but they're almost product experts de facto and then they'll come in and sell a complex piece of developer software or contact software or analytics software or security software and they will melt because it's more complicated. So try to find folks that have sold in a harder environment and watch them fly.
