From 2022 to 2024, Twilio had a rough ride.
Ultimately, its monster $3.2BN acquisition of Segment sidetracked the businesses from its communications and telephony heritage.
As it did so, Twilio aimed to transform itself into a marketing tool, a sales tool, and more, taking on grand, ambitious ideas that received significant investment.
Eventually, it became the Swiss Army Knife of CX that nobody asked for.
However, as it planted money into these projects, the world adjusted to its post-pandemic new normal, the SaaS market slipped, and it just wasn't the time to be non-profitable.
The result? Twilio got pummelled.
In May 2023, it recorded $1.38BN in annual net losses. Later, it announced numerous rounds of layoffs and sold off multiple business units, including its IoT arm.
Activist pressure eventually consumed the business, and – in January 2024 - Jeff Lawson, Founder & Former CEO of Twilio, left in a shroud of gloom.
Picking up the pieces, Khozema Shipchandler, CEO of Twilio, had to make a choice: do we sell Segment or make it part of a stronger, more cohesive platform?
Realizing this, he kickstarted a review into its future.
Ultimately, Shipchandler & Co. decided to retain Segment but create more of a bridge between the customer data platform (CDP) and its core communications product offerings.
As such, Twilio started leveraging AI to better align its core product sets and developed playbooks for customers to ensure they achieve value when blending Twilio’s portfolio.
In doing so, Shipchandler believes the company has now carved out a differentiative value proposition.
"We’re uniquely positioned in terms of our core assets," he told Fortt Knox of CNBC.
There’s really nobody that’s got a leading communications capability and a leading data capability. Our ability to then use AI to augment those things is what is going to set us apart.
"We try to take signals from our customers, consider where they are leading us, and create a compelling set of plays that we can put in front of them."




