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The Human Cloud Podcast: Ep. 130 – Stephanie Nadi Olson of We Are Rosie on Pioneering Marketing As We Know It Through Innovative Flexible Talent Models

by | Jun 5, 2024

Stephanie Nadi Olson on The Human Cloud Podcast

Originally posted by The Human Cloud Podcast, June 5, 2024.

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.



00:00 – Introduction and Background

03:03 – The Evolution of We Are Rosie

05:56 – The Client Experience

10:08 – Building Trust with Clients

15:01 – The Role of Leadership in Freelance Adoption

22:56 – The Importance of a Good Freelancer Onboarding Experience

24:55 – Top-Down Support and Execution

25:46 – The Importance of Top-Down Support

26:14 – The First Journey with Flex Talent

28:03 – Moving into Phase Two

29:17 – The Hook for Flex Talent

30:04 – Consolidation in the Industry

33:13 – Specialist Expertise on Demand

34:02 – Consolidation vs. Disruption

38:28 – Proud Accomplishments

43:14 – The Sacrifices of Entrepreneurship

Follow Up Material & Links

Check out the full episode here.