The Human Cloud Podcast

Leaders, Staffing Industry Analysts (SIA) is the gold standard of research on staffing and workforce solutions. Founded in 1989 by staffing pioneer Peter Yessne, SIA was one of the first to pick up on the rise of the freelance economy and has led the charge in researching its size, growth, key players, and everything related to freelance ever since.  In this episode, we chat with Ursula Williams, President of SIA and Co-Author of Together We Rise, along with Barry Asin, Chief Analyst and former President of SIA. Key takeaways: 1: Out of the $3.8 trillion contingent talent spend, most is allocated to independent contractors, and much of it is unmanaged. 2: SIA first identified the freelance economy as early as 2004 in the form of ‘contingent talent.’  3: SIA started noticing talent platforms around 2010: Tech was the driver for freelance, starting with VMS (vendor management systems), then talent platforms. 5: What’s changed? Talent is now in the driver's seat. 6: There is a clear distinction between the B2B and B2C sides of external talent. 7: We’re still not any closer to agreeing on what to call this space. Listeners will walk away with a tangible understanding of the space, where it’s going, and how to seize the opportunity of freelance as a sourcing strategy or an industry to build in.

Leaders, We’re at a pivotal moment in the world of work. While version 1 of the freelance economy was centered on marketplaces, the current phase, driven by large enterprise companies, is a mix of marketplaces, platforms, and boutique solutions. No one better understands this than Fiverr, an early freelance pioneer that revolutionized freelance services by enabling their marketplace to be a comprehensive hub of freelance services, where customers can pick outcomes rather than a traditional hiring process.  In this episode, Dan Oron discusses Fiverr's transformation from a marketplace to a comprehensive hiring platform, addressing the unique challenges of catering to both solopreneurs and larger enterprises. He underscores the significance of understanding enterprise clients' specific needs and delivering tailored solutions. Dan discusses the importance of flexibility and customization in managing freelance talent, emphasizing that different industries and skill sets demand distinct approaches. Dan also introduces the concept of embedding freelancers within organizations and discusses the emerging role of a Chief Freelance Officer, who facilitates seamless access to talent. He points out the integration of freelance platforms with existing systems and the potential for API calls between different platforms, highlighting Fiverr's ability to bridge the gap between clients and freelancers. The platform simplifies the hiring process, offering a trial period to ensure a good fit. Fiverr recently expanded its product offerings to include a personalized AI assistant, a professional catalog for specific skill sets, and the introduction of hourly contracts. AI is set to enhance the user experience and provide valuable insights, paving the way for significant business growth and efficiency in the freelancing landscape. Key takeaways: Fiverr has evolved from a marketplace to a hiring platform, expanding its offerings to meet the unique needs of solopreneurs and larger businesses. Enterprise clients require more specific solutions and tools to manage freelance talent, such as account management and project management. The concept of embedding freelancers within organizations is becoming more prevalent, allowing businesses to access specific expertise and scale up or down as needed. A Chief Freelance Officer role can help streamline the process of accessing and managing freelance talent within an organization. Integration between freelance platforms and existing systems, such as VMSs and MSPs, can enhance efficiency and collaboration. API calls between different platforms can facilitate seamless data exchange and improve the overall freelance experience. Fiverr connects clients with freelancers, making it easier to find the right talent for specific needs. The platform simplifies the hiring process and allows for a trial period to evaluate if there is a good fit. Fiverr is expanding its product offerings to include a personalized AI assistant, a professional catalog for specific skill sets, and the introduction of hourly contracts. AI is being used to enhance the user experience and provide valuable insights. The future of freelancing and AI integration holds great business growth and efficiency potential.

Leaders, today we’re joined by Tyler Denk, Co-Founder and CEO of Beehiiv, one of the leading and fastest growing newsletter software companies. Beehiiv raised a $12.5 million Series A in 2023 and has been growing rapidly, with over $1 million in monthly revenue, according to Tyler.  In this episode, we’ll dig into why Tyler started Beehiiv, what led to their extraordinary success, and what’s next for Beehiiv and the solopreneur industry.   As freelance leaders, our roles often align more closely with those of founders than traditional employees. Whether you’re a VP leading a freelance program, a CEO of a talent platform, or a freelancer, we can all learn immensely from Tyler.  Key takeaways: 1: Founder market fit is the secret ingredient for entrepreneurial success, and can be defined by subject matter expertise. In Tyler’s case, his subject matter expertise came from his time growing Morning Brew as a leading newsletter. 2: Entrepreneurship never stops feeling like the house can fall at any time 3: Product management is tough to explain, yet crucial in growing a company. Being a good product leader means being able to be directionally correct, prioritizing the right roadmap, and tightening the feedback loop to iterate quickly based on informed insights rather than reacting to every piece of data.

Leaders, We know this past month has been fractional heavy. The reason is that fractional is rapidly taking hold across the US, Europe, and Asia. In this episode, John Arms discusses the rise of fractional leadership and its value in solving specific problems within organizations. John emphasizes the limitations of full-time positions and the decline of single job loyalty in today's workforce. John touches on the foundational requirements for being a successful fractional professional and how Voyageur University, a global leader in Fractional Talent education, helps Fractional professionals and businesses who hire them. We discuss the future of fractional work and the infrastructure needed to support it, as well as the centers of gravity in the fractional community. John emphasizes the shift towards value and problem-solving and the return of self-determination in the world of fractional work. Key takeaways: Fractional leadership provides specialized and flexible solutions to specific problems within organizations. Full-time positions often lack the necessary leadership and expertise to address complex challenges. The decline of single job loyalty and the rise of the solopreneurship has contributed to the demand for fractional leadership. Meetings are often unproductive and time-consuming, and fractional leaders can help organizations avoid unnecessary meetings. Incremental measures may not be connected to long-term impact in fractional work. The number of fractional professionals is growing rapidly, indicating a rising demand for their services. Markers for identifying successful fractional professionals include time in the market, wisdom, and a community mindset. The future of fractional work lies in the development of infrastructure and platforms that connect supply and demand. Fractional work emphasizes value and problem-solving over traditional employment models. Self-determination and the pursuit of freedom are key aspects of fractional work.

Leaders, Today we’re joined by Quentin Cloarec, Co-Founder and CEO of Trees Engineering, South East Asia’s leading Engineering Talent Platform. We discuss why Quentin started Trees Engineering, why clients are adopting their unique freelance model, and what leaders can learn from Quentin’s journey.  Quentin embodies two of the biggest trends in the freelance economy: The power of niche, specialized, freelance marketplaces; in his case an engineering talent platform. The global adoption of the freelance economy, with Quentin representing the growth of Southeast Asia and carrying these learnings into regions like the Middle East.    Key takeaways: Why Quentin went beyond a large, horizontal marketplace to solve his own problem within Engineering services How freelance adoption in South East Asia is mirroring the United States   How Quentin scaled their go to market  The value of being incremental versus the traditional view of disruption How large companies have embraced Trees Engineering Big wins, specifically how they enabled a Malaysian regional office to win business from HQ How it’s bigger than freelance, in his case, it’s about fixing the global energy crisis

Leaders, Karina Mikhli is a seasoned Fractional COO and the Founder of Fractionals United. Fractional is one of the most exciting aspects of the freelance economy. Instead of traditional, individual contributor freelance work, fractional unlocks executive level and strategic level engagements and professionals.  According to Human Cloud’s Industry Landscape, there are over 20 fractional focused solutions, spanning sales, marketing, and consulting.  Fractional is also global. The US seems to be first in terms of fractional adoption. But Europe and Asia are quickly catching up. In this episode, we’ll dive into everything fractional. We’ll define who fractional individuals are, what they do, how they differ from traditional freelancers, who they serve, how they work with clients, and what the future of fractional looks like according to Karina.   Key Takeaways: Growth of Fractional Work: The trend of fractional work is on the rise, with more professionals opting for fractional roles to leverage their expertise. Profile of Fractional Professionals: Typically, these individuals are experienced leaders who drive strategic initiatives and produce impactful results. Supportive Infrastructure: The fractional economy is supported by various platforms, marketplaces, and resources that facilitate the work of fractional professionals. Diverse Engagement Structures: Like freelance, fractional can take many different engagement structures. Importance of Communication: Effective communication and clear expectation-setting are critical for successful client engagements in a fractional capacity. Future Outlook: The future of fractional work is promising, with an expected growth in communities and associations dedicated to supporting fractional professionals. Get Involved: Future events and communities for individuals interested in fractional.

Leaders, Today, we have an exceptional guest, Rich Wilson, Co-Founder and CEO of Gigged.AI. Gigged.AI has been around for about three years, raising over $2 million, and is a fascinating use case as a technology-driven facilitator of freelance outcomes, differentiating from traditional marketplaces. In this episode, we dive into some key insights: 1. Technology as a Primary Driver: Gigged.AI stands out by making technology the core of their platform, which is not typical in the freelance space. For most platforms, technology plays a supportive role, but for Gigged.AI, it's the cornerstone of their success. Rich emphasizes that without their advanced tech, the company wouldn't exist. 2. Venture Funding: Unlike many freelance platforms that bootstrap and scale through the founding team, Gigged.AI needed venture funding. With three years of runway and two years dedicated to building their technology, venture funding was crucial for their survival and growth. 3. Enterprise Market Entry: Rich shares strategic insights on supporting enterprise accounts. Gigged.AI uses two specific strategies: enabling internal talent marketplaces and providing speed and customization for end users.

Leaders, In this episode, Henning Schwinum, Co-Founder and Managing Partner at Vendux, discusses the challenges and opportunities of fractional sales leadership. Vendux helps companies grow their sales leadership capital by matching you with a sales leader and team necessary to transform your sales strategy. Henning brings a unique, process-oriented approach to sales leadership. This episode is not just about hiring freelancers; it's about fundamentally transforming your organization and driving growth through efficiency. He shares insights on scoping engagements, the business model, and the success of fractional executives. Henning also addresses common objections and defines the space between fractional and freelance work. He highlights the importance of industry expertise and the value of fractional sales leaders in small to mid-sized companies. Henning also discusses the benefits of external expertise and the limitations of full-time employees in certain scenarios.

Leaders, it’s no secret that Enterprise adoption is tough. Specifically, enabling large companies to scale their freelance spend similar to how external talent is already over 50% of talent within most companies. It’s also getting increasingly blurred with the existing external talent ecosystem. Leaders face tough questions, such as, should external talent programs be different from freelance talent programs? Should talent platforms integrate with VMS and MSP suppliers? Is freelance competitive, or complementary to the contingent talent space? Today we have Colin McDonagh, is a 10+ year veteran in helping large companies scale external talent programs. He is our go-to when it comes to the evolution of external talent, and how freelance is the same, or different from the existing external talent ecosystem. Colin recently joined Worksome as their Head of Enterprise Workforce Strategy.  Colin has extensive experience with successful contingent talent brands. He has served as Global Program Manager for contractor programs at Meta, formerly Facebook, Director at Allegis, helping clients such as Microsoft, and as an advisor at Utmost, which was acquired by Beeline in 2022. He’s also been an early champion of innovative solutions like direct sourcing.  Key takeaways: 1: Where does freelance sit within the greater external talent ecosystem 2: What’s the difference between freelance and gig, freelance and contingent, and can freelance work within the confines of contingent talent   3: Why aren’t we as far along as we thought we’d be 10 years ago  4: Why aren’t there internal freelance roles when companies are spending over $2 trillion dollars globally on freelancers

Leaders,  We all know Enterprise adoption is the biggest barrier facing the freelance economy today. While freelance as a talent source is globally recognized, we’re still in the first inning of the maturity of freelance as an industry. Unlike Uber or other B2C based startups, freelance as an industry looks more like a B2B professional service transformation than a venture backed technology industry. The impact is that instead of overnight adoption, industry maturity is a long, mostly linear process.  Which is why today’s guest is so perfect.  Jeff Fenigstein has scaled marketing freelancers across marketing teams for large companies. First at Woodruff Sawyer, and now as the founder of Market Growth. Specifically, Jeff knows how freelance can be a strategic sourcing strategy that creates dream teams rather than looking at freelancers as transactional contractors that “plug a hole” or “fill a gap”.  In this episode, we’ll get into why Jeff turned to freelance, what his use cases were, and how he overcame the organizational bureaucracy that stands in the way of so many freelance leaders. He also shares his experiences with freelance adoption in different environments, such as startups and enterprise organizations. Jeff emphasizes the need for internal champions and effective communication to overcome hurdles and successfully integrate freelancers into an enterprise. He recommends that enterprise leaders explore freelance platforms, try small projects, and educate themselves on the benefits and possibilities of freelance work. Key takeaways: Freelancers can help businesses accomplish more and reach their goals by providing specific skills and capacity when needed. Using freelance platforms offers access to top talent, faster hiring processes, and the ability to try before committing to a long-term hire. Freelance adoption is different depending on the environments, such as startups and enterprise organizations.  In the Enterprise, freelance adoption requires internal champions and effective communication. To get started, Enterprise leaders should try small projects.