The Data-driven Marketing Challenge: What I've Learned from a Career in the Trenches
- Jennifer Leonard
- May 9
- 5 min read
Updated: Jun 10

The Wall We Keep Hitting
Throughout my marketing career, no matter what the size of the business, I've repeatedly encountered the same problems with data definition and inaccessibility. How can you truly create personalization at scale, when you can't use what you can't see?
I've watched talented teams pour time and energy into personalization efforts, creating messaging templates with different messages for potential use case scenarios, and elaborate branching logic. But without clean, connected data and clearly defined signals, they hit a wall.
What does a successful customer look like, or what are the indicators they are about to churn? No one can agree on what this looks like. Product teams focus on active users via login rates, success teams focus on feature adoption, and finance focuses on renewal metrics and revenue. Marketers try to piece together disconnected views to understand which customers really need attention. It's pretty frustrating to not be able to help customers when they need it most.
When conducting customer journey work, I'm able to document CX and comms throughout the funnel. By interviewing cross-functional teams, I've been able to identify key issues and gaps. Marketing and product teams share research on needs and barriers. Sales and support teams, who are closest to customers, go into detail about challenges and frustrations, or the lack of tools and resources.
But, when I ask "What makes a customer successful?" The most common answer I hear is, "That's the million dollar question!"
It's not a new problem. It's not even a technology problem. It's a foundational problem that continues to hold marketing teams back and needs to be addressed if AI is to truly transform our data-driven marketing efforts.
What This Looks Like in Real Life
Here's what I've seen in most organizations:
Finance owns transaction data. They track purchase patterns, revenue metrics, and financial indicators. All of these are crucial signals of customer health that rarely make it into marketing systems in real time.
Product teams own usage data. They monitor feature adoption, time-in-product, and engagement patterns. This vital information typically lives in product analytics platforms disconnected from marketing automation.
Support teams hold interaction data. They document customer challenges, satisfaction metrics, and resolution rates. These critical indicators seldom inform proactive marketing outreach.
Meanwhile, marketing teams are expected to deliver personalized, timely, relevant communications without comprehensive access to these vital data sources.
Sound familiar?
The result is generic campaigns sent to broad segments, missed data-driven marketing opportunities for meaningful engagement, and frustrated customers wondering why the heck brands they interact with don't seem to understand them.
Why We Can't Just Throw AI at the Problem
As a marketer, I feel inundated by AI. Everywhere I turn, there's another tool promising marketing miracles. Organizations are rushing to integrate AI solutions, and there's this pressure that if you're not keeping up, you'll be left behind.
It's overwhelming, and I'm guessing I’m not alone in feeling this same mix of pressure, skepticism, and information overload. It’s implied AI is supposed to be the answer to all our marketing challenges. I disagree.
Hear me out. I don't doubt AI's potential, but I also believe AI is only as good as the data it's built on.
In environments with fragmented data, artificial intelligence isn't a magic solution. It's actually at a distinct disadvantage. The gap between AI's promise and most organizations' data reality is where the risk lives.
AI requires clean, connected data to identify patterns and make accurate predictions. Without that foundation, even the most sophisticated algorithms will struggle to deliver meaningful insights. It's the classic "garbage in, garbage out" scenario, just with more expensive technology.
Based on everything I've observed in marketing organizations, I feel like investing in AI-powered tools without addressing underlying data problems can lead to disappointment. The technology itself might be excellent, but won't be able to overcome poor data foundations.
We need to fix the foundation first.
The Possibilities When We Get It Right
I do believe AI has transformative potential for marketing teams. But only if we address the fundamental data challenges first. Here's what's possible when we get it right:
Customer Success Prediction: What if we could identify patterns among our most valuable customers and use those insights to guide others along similar paths? Through targeted messaging, in-product guidance, or proactive outreach, we could help more customers find value faster.
Churn Prevention: Imagine recognizing behavioral signals that precede customer departure weeks or months in advance. This would give us time to intervene with precisely tailored retention efforts before it's too late.
Adoption Acceleration: What if we could automatically identify customers who would benefit from specific features based on their usage patterns and business needs? We could guide them toward adoption through personalized communication rather than generic feature announcements.
Content Intelligence: Consider how AI could scan your organization's content ecosystem, automatically identifying outdated materials, surfacing relevant resources for campaigns, and ensuring consistency across touch points. No more manually hunting for the latest product specs or wondering if that case study is still accurate.
I'm that kid in a candy store when I think of all of these achievable outcomes.
Where Do We Go From Here?
I've seen firsthand how data-driven insights can transform marketing effectiveness when properly structured and activated. I've also felt the frustration of knowing that the answers exist somewhere in our data, but not being able to access them when and where they're needed.
Over the coming weeks, I'll be sharing a series of articles that explore how marketing teams can:
Assess their current data foundation and identify critical gaps
Break down silos between marketing, product, finance, and support data
Define meaningful customer success metrics that drive business outcomes
Prepare their data infrastructure for effective AI implementation
Balance personalization with privacy and ethical considerations
This isn't about chasing the latest marketing technology trend. It's about making your existing tools and teams more effective by ensuring they have the data foundation they need to succeed.
Let's Talk About Your Data-driven Marketing Challenges
I've created this series because I've experienced many of these data challenges. While I haven't seen organizations completely solve these problems, I have witnessed how even modest improvements in data quality can lead to better customer insights and more targeted campaigns.
I'm genuinely excited about AI's potential to take these successes further by allowing us to identify patterns we couldn't see before and enabling truly relevant customer experiences. The prospect of marketing teams being able to spend more time on strategy rather than struggling with fragmented systems encourages me to pursue this topic even more.
Have you encountered similar challenges in your organization? What data obstacles have prevented your marketing team from reaching its full potential?
Let's start a conversation about transforming our marketing data reality into the actionable resource we know is possible.



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