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Checking-in with Jeff Lawson

May 17, 2026 by Dave Michels

Pre-releasing this video interview for paid TalkingPointz Subscribers.

The video will debut on LinkedIn and TalkingPointz on May 20th, 12:30 ET.

Pre-releasing this video interview for paid TalkingPointz Subscribers.

The video will debut on LinkedIn and TalkingPointz on May 20th, 12:30 ET.

I’ve always admired Jeff Lawson. I vividly remember the first time he tried to explain Twilio to me. As for many others, it took a few lessons to get Twilio, but I quickly knew Jeff Lawson was a visionary. Jeff not only built an amazing company, he also created CPaaS as an entirely new communications segment. After 16 years of running Twilio, Jeff traded his coding gloves for The Onion. It was a witty move, and thanks to Jeff, The Onion is doing well and back in print. 

Moving from a multi-billion-dollar comms powerhouse to a satire publication might seem stranger than fiction, but poetic is probably more accurate. He moved from messaging to the message. One can respect Lawson, Twilio, and The Onion. Satire is an art and a critical form of storytelling. 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. His 2022 opinion of CRM, being "$69 billion failure," remains largely unchanged. For decades, CRM giants promised a dream of unified customer data, but Lawson argues there is plenty of evidence that suggests they failed. 

Lawson shares how Salesforce, a B2B deals tracker, was shoehorned into a broader B2C tool with disastrous results. Companies pay through the nose for the privilege of having their data held hostage. He is now watching Salesforce pivot to what Twilio built years ago. #headless. Lawson is very suspicious of how the CRM industry will deliver headless. He doubts it will be the disruptive alternative that Twilio and others offer. 

Our conversation covers a lot of ground, including the future of human agents, Billio, consumption-based pricing, the speed of height of the current hype cycle, council AI, and even fusion energy. Saving a satire institution and searching for the next fuel source reveals a character of someone who loves new challenges. 

This conversation makes you think: Is your relationship with technology actually serving your well-being, or are you just paying through the nose for hype that fails to deliver?

It was a sad day when Jeff departed Twilio. I would have preferred it if he had stayed. He had more to do there. Twilio just isn't as interesting without him.

Also: TalkingPointz audio podcast with Lawson in 2022.

By Dave Michels

Dave is an independent analyst and founder of TalkingPointz which is focused on enterprise communications. In addition to this (free and paid) content on TalkingPointz, he contributes to industry sites, can be found at major industry events, and provides advisory services to vendors and financial analysts.

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