How to Bridge the Gap Between Sales and Marketing: Lessons from Debbie Kestin Schildkraut
In the latest episode of the Sticky Note Marketing Show, Mary Czarnecki sits down with Debbie Kestin Schildkraut, VP of B2B Marketing for the Association of National Advertisers (ANA), to explore one of the most powerful — and often overlooked — drivers of business success: sales and marketing alignment.
With more than two decades of leadership experience at IBM, CompTIA, and now the ANA, Debbie has seen firsthand how collaboration, customer-centricity, and clarity can transform business outcomes. Her insights shed light on how marketing teams can build stronger connections not just with customers, but also with sales and channel partners — creating a unified force that drives growth.
“Sales and marketing must be allies, not silos.”
1. Great Marketing Starts with the Customer
Debbie emphasizes that everything begins and ends with understanding your customer.
“First of all, really important — start from the customer. What is it that they need to solve for? What is their goal? What’s their objective? Then make sure it’s going to be relevant for them.”
It’s easy for companies to get caught up in their own solutions — focusing on features, advantages, and product superiority. But Debbie reminds us that relevance is more powerful than superiority.
Marketing that resonates starts with empathy — asking the right questions, listening closely, and grounding every campaign in real customer needs.
2. Collaboration Between Sales and Marketing is Non-Negotiable
One of Debbie’s strongest messages is that sales and marketing must be allies, not silos.
“You need sales and marketing people. You need to be friends, you need to be connected. You’re working toward the same goal.”
Sales teams are on the front lines, hearing firsthand what customers are asking for, struggling with, and excited about. That feedback is gold for marketers — helping shape more relevant content, messaging, and campaigns.
And if you’re working with channel partners or resellers, Debbie stresses that they too are part of your frontline. Building a feedback loop across all touchpoints ensures that marketing decisions are informed, not assumed.
3. Make Emerging Technologies Accessible and Human
As a marketing leader who’s worked extensively with AI, blockchain, and other emerging technologies, Debbie knows that new tech can often feel overwhelming.
“Sometimes people find emerging technologies overwhelming, but when you give them contextual examples — what it did and what the impact was — they can start to connect with it and see where it can go.”
The key is context. Marketers should bridge the gap between innovation and understanding — showing practical, human-centered applications rather than technical jargon. This approach not only educates customers but also inspires confidence and curiosity.
4. Inclusivity and Empathy Are Strategic Advantages
Beyond strategy and tech, Debbie’s leadership is deeply rooted in inclusivity and empathy. Her numerous awards — including Cloud Girls Trailblazer of the Year (2024) and Change Leader Award for DEIB — reflect her commitment to advancing diversity and belonging in tech and marketing spaces.
She believes that diverse perspectives fuel creativity and that companies that prioritize inclusivity are better equipped to understand and serve their audiences authentically.
5. Final Takeaway: Build Connection, Not Just Communication
At the heart of Debbie’s message is a simple truth — marketing is about connection. Whether it’s connecting with customers, partners, or internal teams, success lies in listening, collaborating, and continuously learning.
When marketing and sales work hand in hand, anchored by a shared understanding of the customer, organizations don’t just sell better — they serve better.
