Self-serve first: the overlooked but essential paradigm underlying great software companies | by Gokul Rajaram | Medium

“My biggest regret is that our first customer was $1M ACV*,” my friend lamented over coffee the other day. “I wish I could take it back.” “Why? What do you mean?” I asked, perplexed. He is the CEO of a company that recently raised a Series C from great investors, is growing rapidly, has strong customer retention and a top-notch leadership team. I was — to put it mildly — taken aback. “Ever since that first customer, our product, go-to-market, our support model have all been pulled in one direction — high-end enterprise,” he said. “Our first $1M ACV customer forced us to get on the elephant hunting treadmill, and we’ve never been able to get off it. Our board, our employees, everyone expects us to only go after customers that were as large or larger than our first customer.” “And?” I prompted. “And I’ve been watching this new competitor emerge that’s going after the same market as we are, except from the low end. They are tiny but growing rapidly. And it’s too hard for us to compete wit

“My biggest regret is that our first customer was $1M ACV*,” my friend lamented over coffee the other day. “I wish I could take it back.” “Why? What do you mean?” I asked, perplexed. He is the CEO of a company that recently raised a Series C from great investors, is growing rapidly, has strong customer retention and a top-notch leadership team. I was — to put it mildly — taken aback. “Ever since that first customer, our product, go-to-market, our support model have all been pulled in one direction — high-end enterprise,” he said. “Our first $1M ACV customer forced us to get on the elephant hun