In this conversation, Craig reflects on his unconventional path from law to venture capital, before being dropped into his first CEO role during the depths of the dot-com crash. Tasked with effectively shutting down a failing VoIP company, he instead rebuilt it from the ground up - cutting costs, reinventing the business model, and ultimately selling the company to Yahoo.
That hard-won experience set the foundation for what came next: founding GrandCentral, the startup that would later become Google Voice. Craig walks through how a small team, a bold product vision, and perfect timing led to an acquisition by Google in just 18 months, and his experience scaling a startup product inside a 20,000-person company.
Craig shares how his frustration with outdated enterprise phone systems led him to reimagine business communications for the cloud with Dialpad, years before remote work became the norm. He explains their long-term vision for a unified communications platform, why small, empowered teams outperform bloated organizations, and how the company quietly got a head start in AI long before it became fashionable.
Craig also makes a bold claim: traditional customer experience, as we know it, is dead. He unpacks why agentic AI will fundamentally reshape CX, and how human-AI collaboration (not full automation) will define the next era of enterprise software.
Whether you’re a founder navigating scale, a product leader building for the enterprise, or an operator trying to separate real AI innovation from hype, this episode delivers first-hand insights from someone who’s been on the frontlines of multiple technology waves.
This is the story of a builder who has repeatedly crossed from one side of the table to the other, learning when to grind, when to refocus, and when to place the next big bet.
Share this episode with a founder, operator, or tech leader who’s thinking about scale, platforms, and what comes after generative AI.
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