Insider Lite: Happy New 2024! (Twilio, Intermedia, Calabrio)

by Dave Michels

Happy new year, now get back to work.

This is the Insider Lite – the free post/newsletter (unlike the Insider Report, which hides behind a paywall). My NY resolution is to publish more Lite posts in 2024.

The first big story of the year is a new CEO at Twilio. I was hoping we could avoid this one.

Twilio promoted Khozema Shipchandler, as its new CEO. Shipchandler succeeds Jeff Lawson, the company’s co-founder, who is stepping down as CEO and board member. The company also expects to exceed its outlook for Q4 and FY23.

It’s tragic when a founder is voted out. That didn’t quite happen in this case, but the threat was real. The activist investors were Legion and Anson Funds, and they only held about $40-$50M of the stock each.  Lawson had a hell of a run, though. He founded a company 15 years ago, and the world had never seen anything like it. He’s fought off software giants and carriers, and his efforts created a new Gartner MQ where Twilio occupies the top right. 

I like to think Jeff was tired and chose not to fight. The past few years have been exhausting. When the pirates insist on a plank walk, sometimes a swan dive is appropriate. Twilio’s stock has dropped by 90% since early 2021. His super-voting shares expired (his voting power shrank from 21.8% to 3.7%) last June. He has more competitors on the trad CPaaS side than ever, and his pivot up the stack requires much more capital in a dry market. He just did his third round of layoffs, and he’s been dismembering his company with asset sales and shutdowns. To the ungrateful investors: “Have fun storming the castle.” 

Financial analysts and industry analysts look at companies very differently. The stock went up 7.5% on the news of Jeff’s departure, but the company’s long-term opportunity diminished by much more. CPaaS is a race to the bottom, so you better have low costs or a powerful bundle — and there lies the rub. Jeff was counting on free money to build hooks with Flex, Segment, and other data-intensive applications. Shipchandler is the logical successor, but he will be under equal pressure with less experience and vision. 

Jeff is too young and too smart to hang up his coding gloves. Maybe he will reunite with Bezos at Blue Origin. Perhaps, like Jobs, he will eventually return to Twilio and finish what he started. I can’t wait to see what Jeff builds next.

Calabrio acquired Wysdom, an AI Virtual Assistant platform out of Ontario, Canada. I think the minute of standalone virtual agent companies has passed. CCaaS and WEM are already consolidating.  Right now, the WEM pure-play providers are interesting acquisition candidates themselves, so adding a virtual agent capability may be counter-intuitive. On the other hand, adding AI anything – particularly skills and experience makes sense. This wasn’t likely a big investment, so I’ll bot to that.

Wysdom supports AI-guided solutions to connect to customers, answer equations, complete purchases, and transact any time with a cognitive enterprise care solution over social, web chat, and IVR. Expected to be available in Q2-24. The new bots do not replace or require other Calabrio products.

Intermedia AI: Intermedia launched its generative AI assistant for its Unite communications and collaboration platform to enhance business productivity. The solution is embedded within the chat interface of the Unite mobile and desktop apps. Unite AI Assistant can help draft emails, memos, or other content, summarize data, or assist with research. This is possibly the first generative AI assistant designed to be rebranded. 

These are the kinds of summaries you get in a paid TalkingPointz subscription. People say it’s the best value in enterprise comms. Topics from the last newsletter include Google Gemini, Twitter a year later, annual reflections on the state of meetings, telephony, CX, CPaaS, and more. Updates from Sprinklr, NICE, and Vyopta. Leadership changes, including CK and Vlad. And 11 Good Reads recommendations. Personal and professional subscriptions are available at

Upcoming TalkingPointz Research note (to subscribers only) is on UCaaS Events AKA Hybrid  Events. These solutions go beyond webinars and represent a significant growth opportunity for the UCaaS sector.