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James Regan, CEO of Clutch, joins Bob to unpack what he learned leading some of the earliest generative AI deployments inside California state government under Governor Newsom's 2023 executive order. James traces his path from public health in Health and Human Services to Deputy Secretary for Workforce Development, and explains how procurement and change management had to be ...


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Bob sits down with Erika Oliver, Founder and Managing Director of NewtonHaus and Executive Analyst at Aptitude Research, for a wide ranging look at where AI is really landing in HR and the workforce. Erika shares her non-linear path through executive search and coaching, an unexpected pivot into labor market intelligence, and a moment that reset her priorities and sharpened h...


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Gerry Crispin, founder of CareerXroads and a five-decade veteran of the talent industry, joins Bob to trace recruiting's evolution from paper resumes and fax machines to today's AI-driven hiring landscape. Gerry reflects on the origins of CareerXroads as a trusted peer community built on open sharing rather than competition, and explains why he sees knowledge hoarding as a lo...


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Andrew Brooks, CEO and Founder of Contextual.io, joins Bob to trace a career that runs from early-internet consulting through three exits (Seven Space to Sun Microsystems, a marketing company to ReachLocal, and SmartThings to Samsung) before landing on AI. Andrew explains Contextual's "own your AI" philosophy, why businesses should design, build, and operate their own systems...


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Katherine von Jan (KVJ), CEO and Co-founder of Tough Day and a longtime innovation leader across Lotus Development, IBM, Salesforce, and multiple startups, joins Bob to trace a career built on one consistent thread: putting culture and human potential at the center of technology. The conversation covers the perils of workforce surveillance AI, why "human in the loop" has beco...


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