In this episode of The Room Podcast, hosts Claudia Laurie and Madison McIlwain sit down with serial entrepreneur Craig Walker, founder and CEO of Dialpad.

Craig’s story begins in Cupertino, back when apricot orchards defined the neighborhood and a young Steve Jobs lived just a few houses down. From those early days in Silicon Valley, Craig went on to earn degrees from Berkeley and Georgetown before starting his career as an M&A lawyer advising Cisco, Kleiner Perkins, and Sequoia. That legal lens shaped his entrepreneurial instincts and prepared him for the rollercoaster ride of building companies through both downturns and booms.

Craig shares the pivotal moments behind:

• Rescuing Dialpad Communications in the wake of the dot-com crash, cutting $3M in monthly burn down to $100K.
• Founding GrandCentral, which became Google Voice after its acquisition by Google in 2007.
• Launching UberConference, later rebranded as Dialpad Meetings, and returning to his passion for modern communications.

We dive deep into how Dialpad became an AI-native platform, from the bold $50M acquisition of TalkIQ in 2018 to pioneering real-time transcription, sentiment analysis, and call coaching. Craig explains why “work isn’t a place, it’s what you do” has been his guiding philosophy—and how that mindset shaped Dialpad’s remote-friendly, AI-first culture long before the pandemic.

The conversation also covers:

• What it means to build an AI-native company vs. bolting on AI features.
• Lessons for founders raising capital in today’s market.
• How to balance automation with maintaining authentic human connection.
• Craig’s vision for the future of Dialpad and AI-powered work.
• The woman in Craig’s professional journey who has had a profound impact.

This is a masterclass in resilience, reinvention, and leading at the edge of technological change