Podcast Summary: Marketing Trends

Episode: CMOs Are Hiring Fiverr Freelancers? Find out why.
Host: Stephanie Postles
Guest: Shiri Hellman, VP of Global Brand Communications at Fiverr
Date: November 12, 2025

Episode Overview

This episode dives into the evolving landscape of freelance work, exploring how enterprise brands and top CMOs are increasingly relying on Fiverr freelancers for complex, high-value projects. Host Stephanie Postles and guest Shiri Hellman unpack the latest marketing campaigns crafted with Fiverr talent, discuss trends in AI and the future of work, and reveal insights into organizational shifts as brands adapt to a more agile, hybrid workforce.

Key Discussion Points & Insights

1. The Changing Face of Freelancing on Fiverr

• Weirdest Requests Then and Now ([00:05–03:32])
  • Early Fiverr days saw requests for spells and hugs; now, the platform is much more business-focused, hosting experts from Harvard genealogists to fashion execs offering color matching.
  • “We had a Harvard graduate that was helping people find their family tree, or a senior executive from a fashion brand that was offering his color matching skills…” –Shiri Hellman [00:16]
• Freelancers often become well-guarded "gems" that businesses don’t want to share, reflecting their value and uniqueness ([00:55], [06:12]).

2. Fiverr’s Approach to Creative Campaigns

• Recent Standout Campaigns ([04:07–06:12], [10:57–16:47])
  • Recent videos and campaigns, like the AI-driven "Gary" ad, are often created by Fiverr freelancers themselves, highlighting the capabilities of the platform community.
  • Humorous, edgy, and innovative content is balanced with strategic brand messaging. Campaign concepts originate from Fiverr’s internal teams but always integrate freelancers’ expertise.
  • Quote: “Everything we do is always together with that community.” –Shiri Hellman [05:22]
• Risk-Taking and Edginess
  • Fiverr embraces risks in creative work, grounded in genuine insight and cultural relevance, not just shock-value ([17:47]).
  • “We like to take risks… Even when we're being edgy with our language, it's always rooted in true insight.” –Shiri Hellman [17:47]

3. Finding and Managing Top Freelancers

• Selection Process & Tips ([07:40–09:52])
  • Fiverr’s algorithm matches clients to freelancers using deep data—reviews, communication, deliverables, etc.
  • Pro tier offers rigorously vetted talent for higher complexity; the team also seeks rising stars.
  • “The whole brain behind Fiverr is this algorithm that knows how to rank the freelancer… based on data on each interaction…” –Shiri Hellman [09:00]
  • Recommendations: Look for a balance of established pros and emerging creatives, review portfolios, and consider algorithmic rankings.

4. Organizational Lessons & Team Culture

• Learning from Failure & Embracing Business Courage ([20:07–22:51])
  • Internal "fuck up nights" celebrate bold bets, even failed ones, to cultivate resilience and courage.
  • Notable Quote: “Marketeers are from Mars. Consumers are from New Jersey.” –Shiri Hellman [21:41]
  • Ensuring creative teams stay grounded: “I remind them that they are people… if you don't like this, don't post it.” –Shiri Hellman [23:23]

5. Spotting and Fostering Trends

• Real-Time Marketplace Insights ([25:02–28:11])
  • Fiverr is positioned to identify trending roles by monitoring both supply and demand—searches for novel skills trigger new categories.
  • Examples: Rise of “geo” (Generative Engine Optimization), LLM optimization experts, and new wave of book publishers.
  • “We catch the trend in the right time, in the right place, and leverage it.” –Shiri Hellman [25:02],[28:11]

6. Enterprise Brands Embracing Hybrid Workforces

• Enterprise Use Cases ([28:49–33:18])
  • Enterprises and startups alike now use Fiverr for complex projects and team builds as market needs shift rapidly.
  • Fiverr provides project management services for complex, multi-freelancer projects: “You have a Fiverr person that can find the right freelancers for your project…” –Shiri Hellman [31:20]
  • The future: More hybrid teams, streamlined onboarding, flexible payment models.

7. SEO, Discoverability & AI-Era Marketing

• How Fiverr Stays Visible ([33:18–37:38])
  • LLMs (like ChatGPT) challenge how brands are found; organic content and external mentions are crucial.
  • Campaigns are designed to spark conversation and third-party references, not just self-promotion.
  • “The power of the brand and what people say about the brand is suddenly even more important than ever.” –Shiri Hellman [33:55]

8. Adapting to Rapid Technological Shifts

• Shiri’s CEO’s Bold Email ([38:03–44:59])
  • Fiverr’s CEO sent a company-wide message: “AI will take all our jobs one day, including mine, if …”
  • The ‘if’ is about failing to adapt: “If we want to stay relevant… we have to learn and try and do things…” –Shiri Hellman [38:47]
  • Emphasis on continuous skill-building, curiosity, and accepting multi-functional roles as the path forward for relevance.

9. Embracing the Human Element Amidst Automation

• The Value of Human Creativity ([44:59–48:10])
  • As automation levels the playing field, uniquely human qualities—creativity, lived experience, curiosity—become differentiators.
  • “You always get the same kind of average thing [from AI]… So I think being creative and curious and having the boldness to try things is probably the most important.” –Shiri Hellman [46:09], [47:15]

10. Leadership and Organizational Flexibility

• Advice for CMOs and Brand Leaders ([48:10–53:01])
  • “Embrace the chaos and learn to be comfortable in the unknown… knowing that you might fail.” –Shiri Hellman [48:20]
  • Teams must act quickly, experiment bravely, and accept that org structure and roles will morph with the environment.

Memorable Quotes

• “I do so much on Fiverr… but I wouldn’t want to share the freelancer I found. No, they’re not going to share it with anybody.” –Shiri Hellman [00:55], [06:12]
• “Fiverr’s essence is the ability to match the right freelancer to the right task… all based on data.” –Shiri Hellman [09:57]
• “Business courage is one of the most important things to have… especially in times like the times we live in today.” –Shiri Hellman [18:59]
• “I remind them that they are people… we are all people… if you don’t like this, don’t post it.” –Shiri Hellman [23:23]
• “If I’m a dinosaur and the ice age is coming, I better learn how to snowboard.” –Shiri Hellman [38:47]
• “Embrace the chaos… you need to be able to move forward in the unknown and place bets.” –Shiri Hellman [48:10]

Timestamps for Key Segments

• Weirdest Fiverr Requests & Marketplace Evolution: [00:05–03:32]
• Notable Campaigns & Creative Process: [04:07–06:12]; [10:57–16:47]
• Freelancer Selection & Vetting: [07:40–09:52]
• Embracing Risk & Learning from Failure: [20:07–22:51]
• Spotting Trends in Real-Time: [25:02–28:11]
• Enterprise Adoption of Freelancers: [28:49–33:18]
• Discoverability & AI Era Marketing: [33:18–37:38]
• CEO’s Email and Culture of Adaptability: [38:03–44:59]
• The Human Edge in the AI Age: [44:59–48:10]
• Leadership Advice: [48:10–53:01]
• Lightning Round (Tools, Inspirations, Books, Advice, Hobbies): [54:53–62:11]

Lightning Round Highlights

• Favorite tools/platforms: VEO, Base 44, and hands-on AI and creative tools (Shiri and her CMO both get hands-on) ([55:04–56:31]).
• Inspiration: Podcasts, audiobooks, and niche topics—understanding what makes people tick ([58:57–60:09]).
• Favorite Book: Shoe Dog by Phil Knight ([60:09–60:23]).
• Advice: “Never be offended. If you want something, get up and say it.” ([57:39])
• Unique hobby: Watching TV—with intention, for learning ([61:24–62:07]).

Episode Takeaways

• Top CMOs and brands are increasingly hiring freelancers from Fiverr for complex, business-critical projects—far beyond small, one-off gigs.
• Fiverr’s core is about blending automation and human creativity, using data-driven algorithms to match the right talent to the right tasks.
• In a volatile world, business courage, speed, and adaptability are at a premium. Teams should embrace risk and understand failure as part of growth.
• The future of work is hybrid: expect a blend of full-timers and freelancers managed flexibly, as both technology and talent needs shift.
• Maintaining the human touch—creativity, humor, insight—will differentiate brands as automation makes basic tasks accessible to all.

For those looking to keep their brand agile, creative, and ahead of the marketing curve, this episode is packed with actionable insights and refreshing candor.