Owning the Room: Samantha Skey on AI, Imposter Syndrome, and Leading with Intention
# 1st-party data
# Analytics
# Artificial Intelligence
# B2B
# B2C
# Data monetization
# Digital Strategy
# Leadership
# Marketing
# Media
# Monetization
# Podcast
# Technology
From the boardroom to the breaking wave, Samantha Skey shares what leadership really demands today.
Heather Holst-Knudsen
When I think about leaders who are not only navigating change but reshaping it with intention, courage, and humanity, Samantha Skey stands out. As CEO of SHE Media, one of the largest women-focused digital publishing networks, reaching over 100 million monthly visitors, Samantha brings extraordinary vision to the intersection of media, technology, and culture.
But what struck me most in our conversation wasn’t just her insight—it was her candor. This episode of the Revenue Room™ podcast became something deeper than a discussion about AI and business models. It became a personal reflection on leadership, identity, and what it really means to create impact in a world that’s moving faster than our institutions can keep up.
From Gaming to Media: A Career Built on Understanding Behavior
Before leading SHE Media, Samantha built her career in the gaming world, a place she credits for honing her obsession with user behavior and motivation. In her words, “Gaming was always about understanding what drives people to take action. That never left me.”
That user-first mindset underpins her approach to media today. For SHE Media, it's about more than just creating viral content or maximizing ad impressions. It’s about building authentic connections with women across life stages and identities and then building monetization strategies that honor, rather than exploit, that trust.
SEE OUR FULL INTERVIEW ON OUR YOUTUBE CHANNEL
The AI Tension: Innovation vs. Survival
One of the most powerful insights from our conversation was Samantha’s candid take on AI:
“AI doesn’t exist without content, but if media companies can’t survive, then AI can’t either.”
She’s right. Generative AI tools are trained on publisher content, yet the current monetization structure rarely rewards that intellectual property. Samantha foresees an entirely new industry emerging around authenticity verification, ensuring consumers and businesses can distinguish real from AI-generated information.
But she doesn’t view AI as all threat. She’s deploying it to streamline operational efficiencies at SHE Media, freeing up her teams to focus on strategy and creativity rather than repetitive tasks. Her lens is both realistic and opportunistic, understanding the limitations while leaning into what’s possible.
The New Publishing Playbook
Under Samantha’s leadership, SHE Media has built a diversified revenue engine:
Owned Brands: Editorial brands like Flow Space, SheKnows, and StyleCaster anchor the portfolio.
Creator Representation: Thousands of independent publishers and creators monetize through She Media’s ad tech and brand partnerships.
She’s proving that niche doesn’t mean small; it means focused, relevant, and actionable—three things every marketer needs now more than ever.
Imposter Syndrome: A Systemic Problem
One of the most powerful takeaways from my conversation with Samantha Skey was her reframing of imposter syndrome. Rather than seeing it as a personal flaw or internal psychological hurdle, Samantha challenges us to recognize it as a systemic issue, a product of environments that subtly or overtly exclude people from belonging.
“Imposter syndrome isn’t just about the individual,” she said. “It’s often about the environment that isn’t ready to receive that leader.”
That hit me hard. As women, particularly Gen X women who were raised to perform, achieve, and never show cracks, it’s easy to internalize doubt as a personal shortcoming. But as Samantha pointed out, the so-called “syndrome” is often a reaction to rooms not designed with us in mind. Sometimes it’s about being the only woman at the table or the only one whose path to leadership didn’t follow a traditional script.
She even suggested dropping the word “syndrome” altogether. Instead, she prefers “imposter phenomenon,” a term that acknowledges the external forces at play. It’s not that you’re broken. It’s that the system you’re in might be.
And that’s why this conversation is so urgent. It reminds us not only to reflect on our own feelings of inadequacy, but to examine how our organizations are built. Are they cultivating psychological safety? Do they allow for diverse leadership styles? Are we holding space for women, and all underrepresented leaders, to show up fully, without needing to “fix” themselves first?
Samantha’s insight was a bold invitation to flip the narrative. If you’ve ever questioned your place in the room, ask whether it was built to include you—then lead the charge to build better rooms.
A Leader Grounded in Humanity
We ended our conversation talking about surfing, her passion outside the boardroom. For Samantha, surfing is a reminder that no matter how powerful we think we are, nature is more powerful. It’s a reminder that we’re not meant to control every force, but to respond with intention. That’s where real transformation begins.
That ethos mirrors her leadership: grounded, adaptive, and in tune with forces bigger than herself.
My Takeaway
If you’re leading a revenue team in media, events, or B2B platforms, Samantha’s insights are a masterclass in leading with data, intuition, and empathy simultaneously. The world is changing with AI, but lasting companies will be built by leaders who harness its power thoughtfully and bring their teams along with them.
Want to hear more from Samantha Skey in person? She’ll be speaking at our exclusive Revenue Room™ Salon on October 7 at the Yale Club in NYC. Senior female executives can request a complimentary invitation here.
Heather Holst-Knudsen is a distinguished figure and expert in the events, media, marketing and technology sectors. Using her extensive experience, she guides clients in adapting to structural economic and market changes, seizing the chance to innovate and evolve. She specializes in digital and data disruption and opportunity, exploring how these overarching factors can impact revenue growth, customer-centricity, operational efficiency, profit margins, and the overall valuation of companies in both public and private markets.
Her journey began at her family business, Thomas Publishing Company, where she honed her skills. She further expanded her expertise by holding positions at early industry giants Miller Freeman, Reed Elsevier, and IDG. Returning to Thomas Publishing, Heather founded and spearheaded Manufacturing Enterprise Communications, an integrated media portfolio connecting buyers and sellers in the manufacturing and technology sectors. Starting in 2015 and spanning the next seven years, she leveraged her expertise as a revenue and business leader in various SaaS businesses, including Feathr, Gleanin, Brella and Edflex.
Heather is deeply passionate about digital innovation, data monetization, and AI and how these strategies fuel revenue growth, profitability, and company valuation. To serve and create value for clients in these areas, she launched H2K Labs, dedicated to generating and leveraging value through data for media, business information, events, and adjacent technology and service markets.
