Chris Crosby @ VenturesCX

The CCaaS Valuation Collapse: How I Called It, and What’s Still Broken

To say I’ve been unpopular in certain circles for the last three years would be an understatement :)

Dec 29, 2025 • Chris Crosby

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Last Mile, First.

If 2024 was the year that I called BS on corporate AI theater, 2025 was the year I yawned and searched for substance elsewhere.

Dec 18, 2025 • Chris Crosby

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August 2025

“Let Me Ask My Supervisor”

Why Every Workflow Has a Kill Switch

Aug 20, 2025 • Chris Crosby

July 2025

The Industrial Deletion Complex

Companies solved every technical problem except the only one that matters: actually listening to what they’ve recorded.

Jul 30, 2025 • Chris Crosby

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Recalibration

Industry transitions are never led by headline-chasers. They’re led by the people willing to rebuild the core of not just the tech stack, but the…

Jul 20, 2025 • Chris Crosby

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June 2025

The Existential Crisis Behind Productizing AI

Before we built our AI coaching tool, we had to confront a harder truth: we hadn’t defined what coaching was.

Jun 20, 2025 • Chris Crosby

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Wrapping-up CCW 2025.

There’s a certain AI numbness and fatigue descending across the industry.

Jun 12, 2025 • Chris Crosby

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The Agent Assist Math Problem: Measuring Everything but Impact

After failing with three clients, we rebuilt Agent Assist from the ground up—focused on the 21% of calls where it actually matters.

Jun 5, 2025 • Chris Crosby

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The AI Demo Your Vendor Hopes You Never Request

Ask your AI vendor for one simple demo: Show me a conversation where your AI completely pukes.

Jun 3, 2025 • Chris Crosby

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The AI Agent Assist Failure You Can’t Unsee

What if agent assist revealed the real problem isn't teaching AI your policies, but having policies worth teaching?

Jun 2, 2025 • Chris Crosby

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April 2025

Announcing, the Great Contact Center Rewrite

#unprecedented

Apr 1, 2025 • Chris Crosby

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February 2025

Just Make It Easy (J-M-I-E)

Startups -> Tattoo this on your forehead.

Feb 7, 2025 • Chris Crosby

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