February 13, 2026 • 3 min read
Twilio Pens a Nine-Figure Megadeal, the Largest in Its History

Director of Content & Market Research
February 13, 2026

Twilio has completed its largest-ever deal, penning a nine-figure contract with a leading marketing automation platform provider.
Khozema Shipchandler, CEO of Twilio, celebrated the milestone during an earnings call, where the company reported revenue growth of 14% year-over-year (YoY).
“During the quarter, our go-to-market team delivered several notable wins, including a nine-figure renewal… the largest deal in Twilio’s history,” said Shipchandler.
While the CEO disclosed little more about the deal, he did share that some of the other big wins included Grubhub, Nestlé, and Sierra.
The latter is just one of many enterprise conversational AI providers turning to Twilio to power the voice infrastructure across its platform.
Alongside the record win, the Sierra deal highlights how Twilio is a beneficiary of AI-driven customer experience providers expanding their portfolios and voice propositions.
If voice does, as many predict, become the primary interface for customer experience, with multi-modal elements, Twilio will continue to gain momentum.
Yet, Twilio isn’t only supporting rival software companies in serving customers; revenue from its own self-service products grew 28% year over year, per Schiphandler.
By combining the company’s communications and data portfolios, the company wants to rival its own install base in transforming customer service experiences.
Twilio’s Edge in Automating Customer Service Experiences
During an interview with The Motley Fool, Schiphandler discussed how the company was well-positioned for the era of AI-led multi-channel experiences and persistent customer memory.
Persistent customer memory is an ongoing challenge that CX designers are struggling to overcome.
Indeed, customers often contact support multiple times for the same issue. Yet, current AI and customer service systems struggle to retain and use prior context effectively.
By linking memory directly to backend systems, like CRM or ticketing databases, the AI can access context safely and under controlled rules. However, AI still misinterprets or misuses context, and brands are battling to balance personalization with accuracy and trustworthiness.
Yet, as it owns the data, communication, and AI layers, Twilio is uniquely positioned to help solve this issue moving forward. That’s part of its vision to be the customer experience layer of the internet.
Twilio Aims to Be the “Customer Experience Layer of the Internet”
As outlined in his Motley Fool interview, Schiphandler’s vision for Twilio is to be “the customer experience layer of the internet.”
To understand that vision, first take a step back. Currently, every company globally already uses a cloud communications provider and a data warehouse. Twilio wants to sit on top.
In doing so, it connects communications tools, surfaces contextual data, and delivers AI frameworks as part of a foundation on which companies can build individualized, connected experiences.
Ultimately, that foundation forms the customer experience layer that includes persistent memory, context, and the ability to deploy customer-facing agents anywhere.
Still, most view Twilio as chiefly a communications provider. However, Schiphandler teased that Twilio has several exciting products that will help connect that layer in a private Beta, and these will come closer into view at Twilio SIGNAL in May.