What I Learned Sitting Down with CEO Christine Shaw
Heather Holst-Knudsen
I still remember the first time I metChristine Shaw. We were both navigating the chaos of COVID - she as the CEO of InvestmentNews, leading a transformation under extraordinary pressure; me guiding leaders through one of the most disruptive eras business has ever seen. Even in that moment, she struck me with a rare blend of calm, clarity, and conviction.
So having her join me on The Revenue Room™ Podcast felt like coming full circle. But what I didn’t expect was just how deeply her insights would resonate about leadership, data, transformation, and the future of associations, media, and events.
WATCH TO FULL EPISODE ON OUR YOUTUBE CHANNEL
Below are my biggest takeaways about what it really takes to lead through disruption today.
1. The moment that transformed how Christine leads through transformation
When I asked Christine about the pivotal moment that shaped her as a leader, she didn’t hesitate: Future PLC.
Penwell, she told me, was highly operationally disciplined—process-driven, numbers-focused, buttoned-up. But joining Future PLC was like stepping into another universe:
A publicly traded, hyper-data-driven, tech-sophisticated machine moving at breakneck speed. Weekly updates. Profit warnings. Constant change. A team fluent in digital tools she’d never seen at that scale.
It rewired her leadership.
It taught her that the pace of transformation isn’t something you “manage," it’s something you learn to ride.
And it revealed a truth more executives need to hear:
If your environment is getting faster and more complex, you must grow at least as fast as your circumstances.
– Christine Shaw
2. “Data creates calm in the storm.” And she’s right.
This line may be my favorite thing Christine said in our entire dialogue. It’s not just a philosophy, it’s a strategy.
Christine explained that data removes the emotional volatility that often derails good decision-making. In legacy environments, people fight for their ideas, their products, even their nostalgic attachment to brands. But data? Data has no ego.
When the data tells the story, the debate changes. It becomes truth-seeking, not turf-protecting.
– Christine Shaw
She shared how at Penwell she created a business data analyst role - a role so effective that she has rebuilt it at every company since. Not finance. Not sales ops. A dedicated function responsible for stitching P&L, CRM, and revenue insights into one coherent narrative.
That position became the bridge between strategy and execution, and it became her secret weapon in building trusted relationships with CFOs.
And it shattered internal resistance, not immediately, but inevitably.
Because once you see clean data, you can’t go back.
3. Inside Naylor: The most complex business model Christine has ever led
When Christine said Naylor was “the most complex business” she’s ever run, I sat up straighter. This woman has led global B2B media, events, and digital platforms. So if this is the most complex?
You pay attention.
Naylor’s model is unlike traditional media or events. It’s a multi-rev-engine ecosystem serving associations, not just their audiences or advertisers.
Associations come to Naylor for:
Member communications (content + monetization)
Career centers and job boards
Association management services (AMC)
AMS technology platforms
Events and sponsorship solutions
Each has its own P&L structure, monetization logic, operational systems, and customer psychology. And Christine is balancing all of it while the association sector is facing the same threats as media and events: AI, shifting audience behaviors, and generational change.
And she’s navigating two customers at once:
The association itself
The advertisers, sponsors, and partners she monetizes on their behalf
That’s not just complexity. That’s multidimensional chess.
4. Innovation in an environment built on tradition
Associations move at a different pace from digital media. They are community-driven, culturally rooted, and often steeped in legacy processes.
But Christine is clear:
You cannot preserve relevance by preserving comfort.
She’s embedding AI into:
internal productivity
member content workflows
career center tools
new audience-value products like their AI-powered newsletter
But she’s equally focused on the education layer because many association leaders still fear AI more than they embrace it.
The real disruption, she says, will come when associations realize technology doesn’t threaten community, it enables it. Year-round, always-on, member-to-member value is exactly where AI can help associations thrive.
5. The convergence of B2B and B2C is already here and AI is accelerating it
Christine and I have both seen firsthand how B2B and B2C models are collapsing into each other.
B2C excels at:
personalization
data sophistication
instantaneous buying signals
B2B excels at:
depth of expertise
niche community
problem-solving content
Christine described Future PLC’s ability to outrank Amazon during Prime Day for certain product categories—because of obsessive data discipline. Imagine bringing that level of predictive intelligence into B2B buying cycles.
That is the future. And it’s coming faster than most companies realize.
6. Preserving vs. transforming after an acquisition: Christine's playbook
Christine summed it up beautifully:
There are three types of acquisitions:
Bolt-ons
Profit plays
Strategic shifts
If it’s strategic, you don’t immediately rip out the legacy systems. You protect the “secret sauce”- because that may be the very thing you’re trying to buy.
If it’s a profit play, speed is everything: harmonize systems, unify CRMs, eliminate redundancy.
But the key is discernment.
Knowing what to protect - and what to dismantle - is what separates accretive growth from expensive failures.
7. Gen Z is changing the workplace and leaders must evolve or be left behind
This part of the conversation surprised many listeners. Christine was honest about how resistant she initially felt toward millennial and Gen Z work styles.
But she learned. And her leadership changed.
Gen Z, she said, isn’t unmotivated, they’re purpose-driven. They want impact, sustainability, and meaning. They want mentorship, human connection, and a culture that sees them.
And they need something we don’t talk about enough: Re-integration into real-world work.
This generation missed internships, in-office experiences, and the “osmosis learning” many of us took for granted. Christine is seeing that many want to be in the office, not for surveillance, but for connection.
She’s right. Loneliness is becoming a structural threat to early-career development.
8. The uncomfortable truth about the future
When I asked Christine what uncomfortable truth leaders must face, she didn’t sugarcoat it:
If you don’t change, you will become irrelevant.
– Christine Shaw
AI is not a trend.
Disruption is not optional.
And clinging to the past is not a strategy.
The leaders who resist will not “lose slowly.” They will lose suddenly.
The ones who lean in - experiment, upskill, challenge their own assumptions - will define the future of associations, media, and events.
Final Reflection
Hosting Christine reaffirmed the mission behind The Revenue Room™ Podcast - to elevate the voices of operators who navigate disruption with intention and execute transformation at the highest level.
Christine embodies the intersection of discipline and disruption. Process and possibility. Data and humanity.
And it’s no surprise that she’s not only a member of Revenue Room™ CXO, but also one of our Executive Advisory Board Members. Christine is exactly the kind of leader this network was built for—bold, curious, data-driven, and deeply committed to lifting an entire industry forward.
Inside Revenue Room™ CXO, she helps shape the conversations that matter: how AI is transforming customer value creation, how data becomes a strategic weapon, how leaders build cultures that can adapt, and how organizations grow with intention, not fear.
And in a world being reshaped by AI and audience behavior faster than ever, leaders like her remind us that the future won’t be won by the biggest organizations but by the most prepared ones.
If you want the full conversation (and trust me, you do), make sure to listen to the full episode on Apple, Spotify, or Amazon.
And if you want to join Christine and me in person, the conversation continues insideRevenue Room™ CXOand live atRevvedUP 2026, March 23–24 in St. Pete, where the future of revenue leadership takes center stage.
