Craig Walker is the founder and CEO of Dialpad, a business communications platform powered by AI. A former M&A lawyer turned serial entrepreneur, Craig previously co-founded GrandCentral (acquired by Google and relaunched as Google Voice) and sold his prior company to Yahoo. In this episode, Craig shares how his career unfolded from door-to-door dictation sales to running a 1,500-person company, and how AI became central to Dialpad’s strategy long before the hype cycle.

Craig opens up about the loneliness of leadership, his bet-the-company acquisition of TalkIQ, and the hardest day of his career when four high-stakes deals all hinged on one phone call. He also explains why he still avoids hiring a COO, how he evaluates executive talent, and why long-term trust is his leadership superpower.

Whether you’re building in AI, navigating founder-operator transitions, or learning to scale without burning out, Craig’s story is packed with hard-earned lessons and honest insights.

Where to find Craig:

Timestamps:

(00:00) Starting in door-to-door sales
(02:54) What Craig learned about grit from early sales jobs
(04:42) From Apple to law school to M&A at Wilson Sonsini
(07:22) How Cisco influenced his approach to acquisitions
(08:32) The founding of GrandCentral and acquisition by Google
(09:12) Leaving Google to build again
(13:22) Why Craig couldn’t stay a middle manager
(14:53) What Dialpad is and how it started
(17:36) Google Ventures’ support and early Dialpad funding
(21:03) What startup life looked like in the pool house
(24:17) Family trade-offs and how Craig stayed connected
(28:23) Acquiring TalkIQ and the AI unlock
(33:37) Why Dialpad was years ahead in AI
(35:09) Lessons from integrating an early-stage acquisition
(37:43) What tech reveals about culture
(39:39) How Craig grew from scrappy founder to CEO
(42:20) Delegating to operators while staying strategic
(43:30) Why hiring executives is so hard
(47:23) How he evaluates cultural fit and long-term potential
(49:26) Loyalty, longevity, and building a trusted leadership team
(50:57) Craig’s moment of truth and the most stressful day of his career
(55:48) What he wishes he knew earlier
(57:46) His advice for founders in the AI era

In this episode, you’ll learn:

How to evaluate and integrate an early-stage acquisition
Why trust and long-term relationships build company resilience
What most founders get wrong about hiring senior executives
Why naivete is an advantage in fast-changing markets
How to stay optimistic in the face of startup volatility
Why Craig empowers teams with autonomy, not layers
How a founder mindset helps navigate economic shocks
What it takes to lead through multiple tech transitions
How to pick colleagues and partners you can grow with for decades

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#98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship

From Start-Up to Grown-Up

#98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship