Cloud Connections 2026 felt like a checkpoint for the cloud communications industry.
Not because the room was downbeat (it wasn’t), but because the conversations were unusually direct. Across the event, the same realities kept surfacing: growth is harder to come by, differentiation is harder to prove, and AI is now simultaneously the biggest opportunity in the market and the biggest source of noise.
Keynote speaker Mike Tessler’s idea of “the Fog” captured it well: a moment where offerings can look interchangeable from the outside, pricing pressure keeps tightening, and buyer confidence depends less on feature lists and more on trust, governance, and outcomes. The consistent message wasn’t “wait for the fog to clear.” It was: pick a lane, build defensible value, and execute.
Here are the 10 takeaways that stood out most from Cloud Connections 2026.
Contents
- 1) The “Knowledge Navigator” moment
- 2) The generalist provider is getting squeezed out
- 3) Data is becoming the product, not just the byproduct
- 4) RAG is the AI architecture enterprises can actually deploy with confidence
- 5) Compliance is moving from obligation to differentiator
- 6) Trust—security and privacy—remains the real adoption bottleneck
- 7) UX is no longer a “nice to have”—it’s a competitive weapon
- 8) The smart money is trying to monetize the stack, not replace it
- 9) M&A and analysts kept coming back to one test: pick a lane
- 10) Routes to market are being rewritten in real time
1) The “Knowledge Navigator” moment
CCA Chairman Clark Peterson opened the day with an Apple concept video predicting AI agents, video conferencing, and digital assistants. The twist: it wasn’t made in 2026. It was made in 1987: nearly four decades before today’s tools caught up.
“This is really the first AI agent,” Peterson told the room. “And if there was anybody who was going to be visionaries for this industry, they’re all sitting in this room right now.”
The broader point: cloud comms is shifting from simply connecting people to orchestrating work. The question now isn’t whether the vision exists—it’s whether the industry can turn it into durable products and business models.
2) The generalist provider is getting squeezed out
Mike Tessler (former BroadSoft CEO and now Managing Partner at True North Advisory) urged the room to make a choice: “Stop chasing everything.”
With feature parity largely in place across major platforms, “generalist” positioning increasingly turns into price competition. Tessler’s push was to choose a lane—vertical, geography, or a specific customer problem—and become meaningfully better than anyone else in that space.
“It’s very reactionary,” Tessler said of the market’s current state. “It’s very difficult to figure out how to get out of the fog… and frankly, for lots of people, the growth hasn’t returned.”
3) Data is becoming the product, not just the byproduct
For years, providers have carried enormous volumes of conversation data across their networks and monetized primarily the transport. That mindset is changing.
The Data is the New Oil and vCon Changes Everything discussions pointed toward a new commercial model: capture conversation data via standards like vCon, structure it, analyze it with AI, and sell insights and outcomes back to customers.
“We’ve got all this content flowing through our networks,” Peterson noted. “We haven’t monetized it, other than charging customers to let it flow.”
4) RAG is the AI architecture enterprises can actually deploy with confidence
In AI Gets Real: How GenAI and RAG Are Reshaping Cloud Communications (Gerry Christensen, Mark Lindsey, Jeffrey Korn, Yusuf Mirza), the emphasis was on Retrieval-Augmented Generation (RAG): keeping generative outputs anchored to approved sources of truth so AI can operate inside real enterprise workflows.
The shift underway is from “AI that can talk” to AI that can answer accurately using your data. That’s what makes enterprise AI deployable at scale—especially inside cloud comms environments.
5) Compliance is moving from obligation to differentiator
Compliance isn’t a tax on innovation but something providers can package, automate, and sell: especially as AI touches more customer interactions and data types.
Relevant sessions included:
- The Next Frontier of Voice & Messaging: AI, Accountability, and Monetizing Compliance (Tom Sheahan, Bill Placke, Jeff Potter, Mark Vange)
- From the Cloud to the Hill: CCA’s Advocacy in Action (Jonathan Marashlian, Michael Pryor, Mark Iannuzzi, Chip Pickering)
Compliance is shifting from a back-office obligation to a front-of-house differentiator—particularly as provenance and accountability become essential in AI-mediated communications.
6) Trust—security and privacy—remains the real adoption bottleneck
The biggest blocker to AI in cloud communications isn’t capability: it’s risk.
The conversation repeatedly returned to whether customers can trust AI with sensitive content, and whether providers can confidently operate inside unclear or evolving regulatory environments.
Security and governance aren’t side quests any more—they’re prerequisites for mainstream AI adoption in UCaaS/CCaaS.
7) UX is no longer a “nice to have”—it’s a competitive weapon
As platforms’ capabilities converge, they are differentiated by how smoothly users can complete real work across voice, collaboration, and customer workflows.
In Beyond the Call: Rethinking UX in Cloud Collaboration (Nicholas Clapper, Sanjay Srinivasan, Sachin Vengurlekar, Joshua Lesavoy, Jason Shawgo), the argument was simple: reduce friction or lose attention.
In a feature-parity market, the “best product” increasingly looks like the one that feels simplest—especially once AI is layered into day-to-day workflows.
8) The smart money is trying to monetize the stack, not replace it
Many providers aren’t trying to replace the dominant collaboration environments. They’re trying to profit by enabling them—voice enablement, integrations, support, governance, and compliance wrapped around platforms customers already standardize on.
This idea surfaced in Monetizing the Stack: Voice-Enabled Teams, Zoom & Webex with CallTower (William Rubio): be essential infrastructure, not just another app.
The takeaway: the monetization battle is shifting down the stack—voice, numbering, compliance, and enterprise integration are where differentiation and margin can still live.
9) M&A and analysts kept coming back to one test: pick a lane
The M&A and analyst sessions underscored that strategic positioning matters more than ever—especially as buyers and investors evaluate defensibility in an AI-accelerated market.
Relevant sessions included:
- Deals, Disruption & the Next Wave: M&A in Cloud Communications (Ari Rabban, Joshua Reilly)
- State of the Cloud: Analyst Perspectives on What’s Now and What’s Next (Irwin Lazar, Matt Townend, Catharine Trebnick, Clark Peterson)
Valuation discussions are increasingly tied to clarity of lane—what a company is (and is not), what moat it has, and how it expects to win as AI changes cost structures and feature differentiation.
10) Routes to market are being rewritten in real time
Go-to-market and partner models are under pressure—especially as AI changes how value is delivered (and therefore how it’s sold and priced).
Relevant sessions included:
- Economics of Partnering (Janet Schijns)
- What Agents Really Want: The Truth About Routes to Market (Janet Schijns, Roger Blohm, Lou DiMuzio, Anita Patel, Chris Dennis)
- Partner Enablement That Actually Enables (Katie Merrill, Amy Bailey, Stephanie Benzik, Randall Meeks)
The industry is no longer treating “channel” as a packaging problem. It’s treating it as a strategy problem—how partners create and capture value as platforms become more AI-driven, more integrated, and harder to differentiate on basic features alone.
