Sherry Wong is a creator entrepreneur with hundreds of thousands of followers across social media and the founder of Roster, an AI hiring platform for the creator economy trusted by some of the world's biggest creators like the Stokes Twins, Jesser, and Preston.
She's been creating content since 2011, back when being a YouTuber wasn't even considered cool. But while scaling her platform, Sherry kept running into the same problem. Hiring. Finding the right video editor, thumbnail designer, or producer was a real headache. So she decided to solve the problem herself.
Unlike traditional hiring platforms like Upwork or Fiverr, Roster uses AI to analyze the type of content you make, your niche, your style, and instantly recommends the best candidates to hire. But the real innovation is the hiring challenge feature. Creators dump raw footage onto the platform, set a timeline, and let thousands of applicants compete by submitting test edits. The winner gets the job offer and a cash prize. When Jesser ran a challenge, he offered a $100,000 job and $2,000 cash to the winner. Over 3,000 people applied.
Sherry breaks down how she added YouTuber to her resume before it was common and how it landed her a job in Singapore, why she's expanding beyond creators to work with B2B companies like Stripe, and how hiring challenges are lowering barriers for hidden talent across 150 countries to get discovered by the world's biggest creators.
She explains:
Why she started creating content in 2011 and how it became the reason she got hired at a $50 million creator economy fund
How Roster's AI analyzes portfolios, niches, and software to match creators with the perfect hires in seconds
Why hiring challenges generate over 3,000 applicants and how they turn hiring into content
How Stripe and other B2B companies are now using Roster because every company is becoming a production house
Why AI is changing job descriptions but not eliminating creative roles entirely
Her number one advice for creators launching companies: just start and don't overthink it
Chapters:
Chapters
00:00:00 Introduction: From Creator to Building Roster
00:00:45 The Early Creator Journey: Starting Before YouTube Was Cool
00:02:25 The Resume That Changed Everything: Adding YouTuber to Her CV
00:07:22 The Hiring Pain Point: Why Creators Struggle to Find Talent
00:09:07 What is Roster: AI-Powered Hiring for the Creator Economy
00:10:17 How the AI Matching Works: Portfolio, Niche, and Style Analysis
00:12:15 The Hiring Challenge Feature: Democratizing Opportunity
00:14:20 Results and Impact: 3,000 Applicants and Life-Changing Opportunities
00:18:58 Working with the Biggest Creators: From Stokes Twins to Dude Perfect
00:19:25 AI's Impact on Creative Jobs: Evolving Roles, Not Eliminating Them
00:26:02 Balancing Creator and Founder: The Reality of Wearing Two Hats
00:22:06 Expanding Beyond Creators: Bringing Roster to Brands and Agencies
00:24:38 The Creator Advantage: Distribution vs Decision Making
00:34:32 What's Next for Roster: Bigger Campaigns and Productions
00:35:10 Final Advice: Just Start and Capitalize on Naive Ambition
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Scott van den Berg
LinkedIn: https://www.linkedin.com/in/scott-van-den-berg-22b534150/
Instagram: https://www.instagram.com/scottvandenberg_/
YouTube: https://www.youtube.com/@scottvandenbergvc
Sherry Wong
Roster: https://www.joinroster.co/
Instagram: https://www.instagram.com/sherrybyw/?hl=en
HotStart VC is a fund that exclusively invests in brands founded by celebrities and creators. We're the go-to platform for celebrities and creators launching brands, providing capital, strategic support, and the infrastructure to scale.
