Checking In with Jeff Lawson

I’ve always admired Jeff Lawson. I vividly remember the first time he tried to explain Twilio to me. He still had hair back then. I will admit that it took me a few of these sessions to understand Twilio, but I knew Jeff was brilliant. Not only did Jeff build an amazing company with a strong culture, but he also created an entirely new segment in communications. After 16 years of running Twilio, including an IPO, Jeff hung up his coding gloves. The next stop, surprising (at first) was The Onion. He shares the story in this interview. Spoiler: The Onion is doing well and back in print. Moving from a multi-billion-dollar comms powerhouse to a satire publication may not seem intuitive. Poetic is a better description as he transitioned from messaging to the message. One can respect Lawson, Twilio, and The Onion — it’s a happy journey. I have always considered satire as a critical form of storytelling. It is one of the hardest forms of comedy because it requires so much awareness. The Onion is an important source of truth, which is more than Jeff would say about CRM. Speaking of CRM, Lawson’s views of CRM haven’t changed. I asked him if his views have changed since SIgnal 2022. Where he declared CRM a "$69 billion failure." Spoiler: No. For decades, CRM giants promised a dream of unified customer data, but Lawson says the evidence speaks for itself. Lawson shares how Salesforce, born as a B2B deals tracker, was shoehorned into a broader B2C CRM tool with disastrous results. He says companies pay through the nose for the privilege of having their data held hostage. He is now watching Salesforce pivot to a #Headless model, similar to what Twilio built years ago. Lawson is very suspicious of how the CRM industry will deliver headless. He doubts it will be the disruptive alternative that’s needed. Our conversation covers a lot of ground, including the future of human agents, the never-launched Billio service, consumption-based pricing, the speed and height of the current hype cycle, council AI, and even fusion energy. As we navigate an era defined by decision fatigue and algorithmic noise, we are left with Lawson’s central provocation: Is your relationship with technology actually serving your well-being, or are you just paying through the nose for hype that fails to deliver?