116 episodes

The Human Cloud Podcast

Where entrepreneurs, investors, and yes...even you corporate warriors meet to talk about the freelance economy.

Each month we bring on an industry leader, corporate leader, and innovator of the month pushing the freelance economy forward.

Led by Matthew Mottola, 10+ year leader in enterprise adoption of freelance workforces, published author, prior venture backed founder and leader of Microsoft’s signature freelance product.

In the words of Matthew, "let our inbox be yours".

The Human Cloud Podcast The Human Cloud Podcast

    • Business

The Human Cloud Podcast

Where entrepreneurs, investors, and yes...even you corporate warriors meet to talk about the freelance economy.

Each month we bring on an industry leader, corporate leader, and innovator of the month pushing the freelance economy forward.

Led by Matthew Mottola, 10+ year leader in enterprise adoption of freelance workforces, published author, prior venture backed founder and leader of Microsoft’s signature freelance product.

In the words of Matthew, "let our inbox be yours".

    Ep. 115: Karina Rehavia, Founder & CEO of Ollo: The Rise of Full-Service Freelance Platforms

    Ep. 115: Karina Rehavia, Founder & CEO of Ollo: The Rise of Full-Service Freelance Platforms

    Karina Rehavia, Founder & CEO of Ollo, is an accomplished entrepreneur and business leader with over 20 years of experience and a proven track record of launching innovative service offerings. She has led several business development and large-scale projects for prominent global organizations. Karina joins us today to discuss the freelance economy and the growth of human cloud platforms like Ollo. She shares the story of launching Ollo and the challenges she faced in building a platform that emphasizes flexibility, high-touch client service, and human intuition in matching clients with creative freelance talent. She highlights Ollo's success in acquiring top clients by providing a full concierge experience beyond just a talent marketplace. Karina also discusses the future of the freelance economy and Ollo's plans for continued expansion, including a new initiative around influencer marketing.

    • 45 min
    Ep. 114: Jason Posel, CEO of Greenlight.ai: Managing Compliance Risks in the Freelance Economy – Deep Dive into USDOL's New Worker Classification Rules

    Ep. 114: Jason Posel, CEO of Greenlight.ai: Managing Compliance Risks in the Freelance Economy – Deep Dive into USDOL's New Worker Classification Rules

    Jason Posel, CEO of Greenlight.ai, is a recognized leader in the Future of Work. He is an expert in managing contingent workforce payroll programs and associated contractor classification, tax, and labor law issues. This conversation explores the topic of worker classification and its impact on the freelance economy and provides timely insights into the potential impact of the recent updates by the U.S. Department of Labor on worker classification. Risk of misclassification is by far one of the leading blockers for freelance adoption, at scale, due to the massive implications of not getting this right. Jason emphasizes the need for a robust process to evaluate and engage contractors and helps companies adapt to these changes, ensuring compliance and fostering a fair and transparent work environment. 

    Takeaways


    Having a robust process to evaluate and engage contractors is crucial for larger enterprises.


    Recent changes in classification legislation have made it harder for businesses to classify workers as independent contractors.


    Companies have traditionally used internal processes, employer of record services, or staffing companies to manage classification.


    The rise of freelance work has introduced new challenges in classification, particularly in terms of compliance and risk management.


    Companies should pay attention to this issue and implement programs to mitigate risks.

    • 47 min
    Ep. 113: Gali Arnon, Chief Business Officer – Marketplace at Fiverr: How AI, Productization, and Technology Is Creating The Future of the Freelance Economy

    Ep. 113: Gali Arnon, Chief Business Officer – Marketplace at Fiverr: How AI, Productization, and Technology Is Creating The Future of the Freelance Economy

    Leaders,





    Gali Arnon, Chief Business Officer – Marketplace, at Fiverr explains why human relationships will become even more important in the age of AI and automation. Touching on her 6+ years at Fiverr, her prior experience leading a range of software companies, and the journey of Fiverr from a startup in 2010 to a leading public company today. Gali will show us why the future of work is more human than ever, and how Fiverr’s focus on product and technology has enabled both freelancers and clients to form deeper collaboration. She’ll discuss the practical applications of how Enterprises are scaling their freelance workforces, with examples from Amazon, Monday.com, and Stripe to name a few, and uncover the transformational benefits these companies have had from the creation of custom marketplaces and integrating freelancers into existing business processes. Last, she’ll let us in on Fiverr’s latest product launches. To no surprise…since Fiverr has historically been the leader in product innovation as they’ve both internally developed or acquired future looking products like the acquisition of And.Co, a freelance operating system that’s now Fiverr Workspace, and Stoke Talent, an Enterprise Freelance Management Suite that’s now Fiverr Enterprise.







    Some key takeaways from this episode:



    Fiverr has had a significant impact on the freelance economy by productizing the process of hiring freelancers and removing friction and bureaucracy from the talent marketplace.



    The future of Fiverr and the freelance economy lies in bridging the talent gap and providing personalized, efficient, and trusted solutions for businesses of all sizes.



    Human talent is irreplaceable and plays a crucial role in creativity, human touch, and uniqueness, even in the age of AI.



    Creating custom marketplaces for enterprise clients allows businesses to integrate freelancers into their existing processes and leverage their expertise to drive growth and innovation.



    Follow the link to learn about Fiverr’s latest product release: https://fvrr.co/3SBv9vj

    • 58 min
    Ep. 112: Consulting 2.0: Insights from Catalant CEO Patrick Petitti

    Ep. 112: Consulting 2.0: Insights from Catalant CEO Patrick Petitti

    Leaders,

    Our guest today is Pat Petitti, Co-Founder & CEO of Catalant, the leader in independent management consulting. For over a decade, Pat has pioneered the transformation of traditional consulting into a more responsive, on-demand model. He's been at the forefront of the freelance economy since founding Catalant in 2012.



    A few key takeaways:



    Pat will go beyond just using the term "freelance" and explain what a freelance workforce enables



    The focus is on transformation - specifically transforming traditional consulting into Consulting 2.0



    The freelance model provides benefits beyond just speed, cost, and quality



    It's more than a staffing or contingent talent model - it enables fundamental organizational change

    • 52 min
    Ep. 111: Brett Trainor: Fractional Leadership Mastery

    Ep. 111: Brett Trainor: Fractional Leadership Mastery

    Brett Trainor is a fractional leader and the Founder of the Corporate Escapee Podcast. He is an expert in one of the fastest growing segments of the freelance economy - Fractional. Brett is helping GenX escape the corporate world and take control of their future without sacrificing income. 

    Some key insights to listen out for in this episode:


    Fractional work represents executive-level leadership - fractional leaders have the experience and expertise of VPs, directors, etc.


    Brett provides tactical advice on what works well for fractional engagements based on his experience, such as building out the infrastructure and processes


    Ideal workflow: Brett breaks down how he operates fractionally - working on hourly, monthly retainer, or outcome-based engagements

    • 53 min
    Ep. 110: Rae Hames, Co-Founder and CEO of Teamera: Improving the impact of flexible teams

    Ep. 110: Rae Hames, Co-Founder and CEO of Teamera: Improving the impact of flexible teams

    Rae Hames is the Co-Founder and CEO of Teamera, a pioneering insights platform revolutionizing how companies build and optimize hybrid teams. With an extensive background that spans 15 years in advertising — including roles as an agency operator, brand-side leader, and freelancer — Rae brings a deep understanding of the operational challenges of managing an increasingly freelance-dominant workforce to the table.





    Before launching Teamera, she co-founded Work Sandy, a freelance staffing consultancy, where she and her team supported major consumer brands build their flexible team infrastructure to improve hiring speed, reduce recruiting costs, and improve team performance. Rae has an impressive ability to create efficient, data-driven flexible teams, specifically by helping leaders create systems that blend full-time employees, agencies, and freelancers under one cohesive unit.





    A couple of highlights from within this episode:




    Why freelancers will never completely replace full-time employees… and why getting the right mix of freelance/full-time talent is critical for businesses today
    How agencies ended up in a “doom loop” that has impacted their profit margins while improving opportunities for freelancers
    The practical challenges of planning freelance teams - and how to optimize them over time
    Rae's advice on how leaders can start building an effective flexible workforce (Hint: all you need is two people - a leader with a strategic vision and a project manager!)

    • 51 min

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