The Human Cloud Podcast

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.

Leaders,In this episode, Jonathan Wolfson, Chief Legal Officer and Policy Director at the Cicero Institute, comprehensively analyzes the freelance economy from legal and governmental perspectives. As we all know, compliance is a massive blocker in adopting freelancers at scale. Jonathan breaks down the policy side of how legislation is influenced, formalized, and leads to compliance regulations. While Jonathan is based in the US, understanding the forces of freelance legislation is applicable globally.More than today’s current legislation, Jonathan will also outline the history of employment law, which was established in the 1940s and does not accommodate today's modern workforce. From this historical perspective, we’ll understand the government's opposition to freelancing.Last, Jonathan will highlight the challenges and opposition to freelancing, the risks and liabilities for businesses, the impact on business transactions, potential solutions and future outlook, the legislative landscape and regulatory changes, and actions individuals can take to make an impact.Key takeaways:  Legislative and regulatory changes are necessary to address the challenges of independent contracting, though the future remains uncertain Current employment laws, dating back to the 1940s, fail to address the modern freelance economy Misconceptions, political motivations, and concerns about tax collection and worker protection fuel opposition to freelancing Businesses face significant risks and liabilities if workers are misclassified as independent contractors

Leaders, the freelance economy is quickly growing from a marketplace dominated industry to a robust ecosystem with 10 different segments.  One of the most fascinating segments is the freelancer focused tools and solutions that enable freelancers to scale their businesses without needing a platform, or in tandem with a platform.  Upside is one of these exciting new startups leading the solopreneur charge. By monetizing referrals, Upside enables freelancers, consultants, solopreneurs, whatever you want to call us, to monetize our network in a way that’s a win-win for us, our clients, and Upside.  In this episode, we’ll open up the hood to why Mike is building Upside, how he got to the insights of starting Upside (hint…he has been in this space for a while), and where he sees the freelance economy going.   You will also meet an incredible founder, Mike Wilner. Before Upside, Mike built a freelance web design marketplace in 2015, Co-Authored the book Oversubscribed, and worked at Amazon Web Services.  Key takeaways: Traditional marketplaces face challenges in retaining top talent and generating demand. Upside is a partnership platform that empowers individuals and small firms in the professional services industry. Successful referrals are the core metric for Upside, enabling users to share opportunities and collaborate. The future of the freelance economy lies in uncapping the potential of individuals and creating infrastructure for collaboration and business development.

Leaders, what if I told you there was a secret talent pool that could revolutionize customer experience? Instant Teams, a CX talent platform specializing in military spouse talent, is that secret solution. Founded by Liza Rodewald and Erica McMannes, Instant Teams is a talent marketplace that enhances customer experience teams by integrating military spouses from their extensive talent community of over 68,000 members across the entire customer experience lifecycle. For industry leaders, here is what’s incredible about Instant Teams - they go beyond a freelance talent marketplace and use freelance models to revolutionize a core business problem - customer experience. Liza and Erica could have easily created a self service talent marketplace that matches military spouses with employers similar to the traditional marketplace model. Instead, they went above and beyond, understanding that a self service marketplace wouldn’t work in this case.  For customer experience leaders, Instant Teams enables a superior customer experience, specifically:  24/7 coverage with US support staff, since military spouses are all over the world High retention, with 7.5% churn compared to the industry standard of 30%+ High customer satisfaction, since military spouses have a wide range of experiences, enabling them to connect with people across vasts parts of the population High quality customer experience use cases, for example customer demo’s, cyber fraud detection, and booking a flight In this episode, we’ll dive into Liza’s journey, the evolution of Instant Teams, the development of customer experience, and her insights on the future of work. We’ll understand:  Why the traditional Business Process Outsourcing model and staffing processes are broken, and how a remote first solution like Instant Teams doesn’t reinvent the wheel, but rather innovates a better solution. Why Instant Teams didn’t build a self service freelance marketplace, instead opting for a talent platform that leverages part time, full time, and team creation capabilities. How customers scale from interested to fully embedded customer experience teams through Instant Teams 3 step process. Some key takeaways: Liza and Erica were uniquely positioned to see this challenge and connect the dots of military spouse capabilities to customer experience. While remote work has been getting slack in the news, remote is a powerful force if harnessed correctly. In Instant Teams case, this level of customer experience wouldn’t be possible through default in person office environments. But it requires founders like Liza and Erica who have both felt the pain, are in the military spouse environment, and know how to combine the right people, processes, and technology to leverage remote work within a customer experience environment. Instant Teams uncovers a massive business model innovation that all freelance platforms can have. In this episode we call it the ‘SaaS-ification’ of talent platforms.  Customers are Partners, and Instant Teams provides a Partner experience and relationship rather than being another vendor. FOUNDER MAGIC - what is it? Why is it MAGIC?

Hooman Radfar, co-founder and CEO of Collective, shares insights from his journey as a tech entrepreneur who sold AddThis to Oracle. He emphasizes the shift towards 'one person, one billion dollar businesses' and the importance of viewing freelancers as founders. Hooman breaks down the complexities of S-Corps and how Collective simplifies financial management for solopreneurs. He also explores the evolving freelance economy and the critical need for community support, encouraging collaboration over isolation in the pursuit of success.

Leaders, Stephanie is one of the pioneers of our industry. If we had a Mount Rushmore, Stephanie would be front and center. She's the founder and chair of the board of We Are Rosie, a leading marketing services company and freelance community that has grown to more than 30,000 "Rosies" and 200+ corporate partners. In 2021, after three years of unbelievable growth, We Are Rosie received a strategic investment from Align Capital Partners (ACP). In this episode, we’ll reflect on the last 6 years of Stephanie’s journey trailblazing the future of marketing. She’ll share the challenges and successes We Are Rosie has faced over the past few years, including shifts in client priorities and the perception of freelance work. We’ll get deep into the importance of trust, and the secrets Stephanie’s found for building strong relationships with both clients and talent. For example, she’ll teach us how she looks at the role of leadership and how important shared responsibility is in successfully adopting freelance talent. Tactically, she’ll teach us how We Are Rosie enables this by creating a positive onboarding experience, ensuring top-down support, and executing an end-to-end flexible talent solution rather than being just another marketplace or just another vendor. Stephanie will also talk about the exact ROI and use cases of flexible talent and teams. She’ll uncover what we mean by “specialist expertise on demand” and discuss the launch of Run by Rosie which manages marketing projects from start to finish. Last, Stephanie will give her predictions on the future of the freelance economy, as well as a warning against excessive consolidation and advocating for vertical expertise.

Elina Jutelyte, the founder of Freelance Business Community, discusses the challenges and opportunities of hosting events and running freelance-based communities. She shares insights on the changing freelance economy and the role of platforms in freelancing. Elina emphasizes the importance of understanding the ROI of community and tailoring it to specific goals. She also provides indicators for companies to consider when investing in community and shares her vision for the future of freelancing. Key Takeaways: - Running events and communities for freelancers can provide valuable connections and support. - Platforms play a role in freelancing, but their effectiveness varies depending on the freelancer's location and industry. - The freelance economy has seen growth and changes, with more acceptance of freelancers and a need for specialized services. - The ROI of community depends on the specific goals and outcomes desired, and tracking engagement and results is crucial. - Indicators for investing in community include demand for content and connections, and the opportunity to fill a niche or address specific needs. - The future of freelancing and community involves increased support and protection for freelancers and the use of technology and AI to enhance connections and content. - During challenging times, community support can be invaluable for freelancers, providing advice, connections, and encouragement. This episode is brought to you by We Are Rosie, a leading flexible talent platform redefining how marketing works. Learn more at https://wearerosie.com