The Human Cloud Podcast

Rich Wilson, CEO & Co-Founder of Gigged.ai, shares how enterprises can achieve true talent access by combining internal mobility, external on-demand talent, and AI agents in a single platform. He explains how Gigged.ai starts small with skills inventories and real projects, builds adoption through hands-on results, and engages procurement early to make scaling easier. Rich also discusses the rise of “bring your own agent,” where companies track both human and AI capabilities side by side, and how subscription-based pricing simplifies enterprise adoption. This episode highlights a practical path to blended talent, helping hiring managers get work done faster while reducing friction across HR, procurement, and technology teams.

Steve Smith, Managing Director of Growth at Rep Cap (former Partner at The Starr Conspiracy), joins Matthew Mottola to talk about the real state of AI, work, and leadership. Steve explains why the job board is dead, how the shift from venture-backed growth to private equity discipline is changing how workplace technology companies operate and hire, and why human connection still drives business in an AI-first world.They discuss how leaders can balance automation with creativity, the rise of small and intimate events over large conferences, and how data, not AI alone, will define the next wave of workforce technology. Steve also shares his perspective on what makes great leaders today, those who can integrate technology and human insight without losing authenticity.

Reena Gupta discusses how organizations can preserve institutional wisdom and make it accessible through digital avatars. As Founder and CEO of Wisdocity, she shares her journey from India to building a successful company in the US, reflecting on the challenges of knowledge capture, change management, and implementation in complex organizations. The conversation explores how technology can enhance education, scale mentorship, and create a services hub that bridges human expertise with digital tools. Reena’s story underscores the power of continuous learning, accessibility, and using technology to make collective wisdom a living asset.

Brian Wallins discusses how AI, automation, and platform innovation are reshaping talent acquisition. As Research Director for Talent Acquisition Technology at SIA, he explains how the explosion of new tools is transforming the staffing industry and why flexible workforce models are now core to enterprise strategy. The conversation explores the ongoing consolidation of technology providers, the structural impact of AI on workforce demand, and how organizations can stay competitive in a rapidly changing market. Brian also reflects on the importance of CollaborationX as a space for leaders to connect, share ideas, and shape the future of how companies find and manage talent.

John Nurthen discusses what SIA’s research reveals about the state of the contingent workforce and how data is shaping the future of work. Drawing from over 240 annual reports, he explains where growth is real, where perceptions are off, and why data comparability remains one of the biggest challenges in workforce analytics. The conversation explores how AI is being applied in workforce management, the importance of ethics and explainability in algorithms, and how research-backed insights are helping organizations navigate a shifting, service-driven economy.

Sandra Pinnavaia, Global Head of On-Demand Talent Strategy & Innovation at Heidrick & Struggles, brings more than 25 years of experience as a business leader, management consultant, and trusted advisor. From her early days in biochemistry and McKinsey to building a freelance consulting practice before the “gig economy” even had a name, Sandra has been at the forefront of how companies access and deploy top talent.In this episode, she explains why demand for interim executives has surged more than 300% since 2020, how “leadership liquidity” helps organizations stay agile in uncertain times, and what leadership assurance means for boards, CFOs, and HR leaders. Sandra also shares why projectizing AI and transformation work is reshaping strategy, and why compensation and culture must evolve to keep pace with today’s flexible, high-impact workforce.

Brian Evergreen discusses the transition from digital to autonomous transformation, emphasizing the need for organizations to envision a future worth solving for. He highlights the role of AI agents in shaping future work environments and the importance of moving beyond traditional digital transformation strategies.

Leaders,Ian Gilbert, SVP Enterprise at Airtm, breaks down how stablecoin payouts and user-owned wallets improve speed, satisfaction, and repeat work.We cover what “Airtm Friendly” means in practice, how to integrate wallet options into legacy systems without piling on friction, and what enterprises miss when they treat payouts as back-office ops.Ian shares lessons from millions of users across the Global South, the realities of freelancers juggling multiple platforms, and Airtm’s path to serving 100 million digital entrepreneurs by 2030.If you're sourcing specialized talent, scaling data work, or trying to pay people in currency that holds value where they live, this one will help you pressure-test your payment stack and find fast, lasting wins.

Leaders,Developer talent is global, but opportunity is not. For our 200th episode, Paul Rios, Head of Revenue Experimentation at Telescoped and former HubSpot leader, breaks down why more companies are turning to Latin America for engineering.We cover the hotspots driving growth, the loyalty and cultural alignment of LATAM talent, and why “will over skill” matters when building product teams. Paul also explains Telescoped’s invite-only TrustRank model, how curated shortlists beat endless resumes, and what an AI-first go-to-market stack looks like in practice.If you want to hire smarter and build faster, this episode shows you how.

Leaders,Anurag Bhalla, Co-Founder and CEO at Outsize, shares his journey from corporate and consulting to building one of the most impactful platforms for independent talent across Asia and Africa. He explains why traditional employment models fall short, how cultural attitudes toward work are shifting, and why companies are turning to flexible, project-based talent to stay competitive.Anurag highlights the rise of the five-to-fifteen-year independent segment, the emotional shift from “I am my company” to “I am my skill,” and how enterprises can build agile workforce models that balance a strong core with flexible capabilities. He also discusses why independents often deliver stronger outcomes than traditional employees and how organizations need to rethink engagement, speed, and incentives to succeed in this new era of work.