Owning the Room: Samantha Skey on AI, Imposter Syndrome, and Leading with Intention
speaker
Samantha Skey is Chief Executive Officer of SHE Media, a top 10 media company reaching 74M monthly unique visitors. SHE Media, including flagship brands SheKnows, Flow Space, StyleCaster, Soaps and TVLine, was acquired by Penske Media Corporation in March 2018.
In addition to the company’s owned and operated brands, the ‘SHE Media Collective’ represents one of the largest networks of independent lifestyle publishers and Creators in the US. Skey launched the SHE Media Collective in 2016 with a focus on supporting under-represented publishers and Creators. The Collective contributes millions of dollars in revenue to independent publishers annually, helping women and minority-led businesses scale both their profits and their social impact.
In 2021, Skey led the launch of SHE Media’s Meaningful Marketplaces (MMP), a community of women and minority-owned publishers and content creators. The “MMP” enables advertisers to buy media at scale from the Collective’s premium publishers, ensuring that independent media receives the economic support to thrive.
Throughout her career, Samantha has exhibited a long-standing commitment to the advancement of equity and inclusion through media. In 2023, Skey led the launch of the SHE Media Co-Lab Whole Life Health at SXSW with a star-studded line-up of experts and thought leaders who brought health innovation to this international stage, earning both a Fierce Pharma and Anthem Award.
In 2023, Skey launched the Flow Space platform for SHE Media. Flow Space is a digital and live media platform providing content, community, and commerce in service of women’s health. It has already garnered recognition, winning an Anthem and a Viddy Gold Award. Flow Space leverages the expertise and scale of the Flow Space Collective, reaching 1/3 of all women 35+ who consume health and wellness content online.
Samantha began her career in digital media and technology over 25 years ago at Interactive Imaginations, a gaming start-up that went public in 1998. She held management roles with CNET, Disney, and Alloy Inc. Prior to joining SHE Media, Skey was Chief Revenue and Marketing Officer for clean tech innovator, RecycleBank, and joined SheKnows in 2013.
SUMMARY
In this episode of *Revenue Room™, Samantha Skey, CEO of She Media, shares her bold, human-centered take on leadership, AI disruption, and the future of digital publishing. From reframing imposter syndrome as a systemic issue to building a diversified media model grounded in authenticity, Samantha offers a masterclass in leading with courage, clarity, and purpose in a time of massive change.
Key Topics Discussed:
-How Samantha approaches leadership with a focus on ethics, empathy, and long-term impact—not just short-term performance. -The tension between AI as an operational asset vs. existential threat to publishers. -Her prediction of a new industry for authenticity verification in content. -Samantha redefined imposter syndrome as a systemic issue, not a personal flaw. -A call to redesign environments to be more inclusive of non-traditional leaders. -She Media’s three-pronged business model: owned brands, creator monetization, and immersive brand partnerships. -The importance of leveraging both quantitative and qualitative inputs to drive business decisions.
About Samantha Skey
Samantha Skey is CEO of SHE Media, a top 10 media company reaching 80 million monthly unique visitors through brands like SheKnows, Flow Space, StyleCaster, Soaps, and TVLine. Acquired by Penske Media Corporation in 2018, SHE Media also operates one of the largest networks of independent lifestyle publishers and creators in the U.S. via the SHE Media Collective, which Skey launched in 2016 to support underrepresented voices. The Collective contributes millions in revenue annually to women- and minority-led publishers.
In 2021, Skey launched Meaningful Marketplaces (MMP), enabling advertisers to scale media buys across the Collective while directly supporting premium independent media. That commitment to equity continued with the 2023 launch of Flow Space, a digital and live media platform focused on women’s health, which won both Anthem and Viddy Gold Awards. Skey also led the debut of the SHE Media Co-Lab Whole Life Health at SXSW, earning accolades from Fierce Pharma and the Anthem Awards.
With over 25 years in digital media and tech, Skey previously held leadership roles at CNET, Disney, and RecycleBank, and joined SheKnows in 2013. She’s been recognized with numerous industry honors, including Ad Age’s “Women to Watch,” Folio’s “Corporate Visionary Award,” and DM News’ “Hall of Femme.” Skey serves on the boards of The Ad Council, World Surf League, and Acast, and is an advisor to Digital Ascendant and Let’s Talk Menopause. She lives in Princeton with her husband and two children and coaches girls’ lacrosse on weekends.
TRANSCRIPT
00:00–02:00 Heather introduces Samantha Skey, CEO of SHE Media, part of the Penske Media Group. Highlights SHE Media's mission: content, commerce, and community at scale for women (88M monthly reach).
02:00–05:00 Samantha shares her unconventional path from international literary scouting to gaming and eventually media. She leaned into roles that connected product and audience—marketing, sales, user behavior. Notes the advantage revenue leaders have in adapting to real-time market feedback.
05:00–08:00 Gaming taught her about fanatical users, behavior insights, and data-driven optimization. Encourages others to lean into AI today like she leaned into digital early on.
08:00–13:00 AI is powerful but threatens publisher monetization. Samantha foresees a new industry around content authenticity and verification. Generative AI tools need quality content, but current models don’t reward IP owners. Discussion on mimicking voices, faces, and digital personas.
13:00–16:00 AI platforms aggregate content without routing traffic or paying royalties. Tools like Perplexity cite sources but compensation is unclear. Advocates for a “music royalty model” for media IP use in AI.
16:00–22:00 Diverse revenue streams: Owned brands (SheKnows, Flow Space, StyleCaster) Independent publisher network (SHE Media Collective) Branded content, display ads, commerce, syndication. Flow Space targets women’s health 40+, science-backed and story-driven.
22:00–26:00 Platforms like Yahoo want brand credibility—AI doesn’t surface it the same way. AI users need better filters to assess content origin. Discusses student use of AI and loopholes around detection tools.
26:00–30:00 Heather and Samantha talk about how AI tools like ChatGPT may weaken creativity and retention. Similar to how Google changed thinking—there's a risk of intellectual atrophy.
30:00–33:00 Samantha explains SHE Media’s fit within Penske's B2B-heavy portfolio. Describes the challenge and opportunity of leading the only consumer-facing brand in the group. Penske’s acquisition of SXSW and strong event strategy.
34:00–39:00 Samantha prefers the term “imposter phenomenon.” Calls it a systemic reflection, not just an internal issue. Asserts that being made to feel like an outsider is often a function of the room—not the individual. Gen X women especially affected due to high-achievement upbringing and fear of failure.
40:00–43:00 Samantha didn’t have a formal mentor, but draws inspiration from a network of smart, purpose-driven friends. Sports (surfing, tennis) offer metaphors and lessons she applies to leadership and life.
43:00–46:00 Surfing is Samantha’s favorite way to unplug; she’s been surfing for 15 years with her husband. They travel to Costa Rica and Montauk to surf—reminder that nature is more powerful and humbling.
46:00–47:00 Books on Her Nightstand The Menopause Brain by Dr. Lisa Mosconi Careless People by Sarah Wynn-Williams Wild Dark Shore by Charlotte McConaghy
