In this episode of How to Ride a Roller Coaster, host David Ezell sits down with Perry Sheraw — a pioneer in marketing automation and customer experience strategy. Long before tools like HubSpot and Klaviyo became industry staples, Perry was building CRM systems from scratch, connecting call centers to digital marketing, and architecting the early blueprints of what we now call customer journey design.
Together, David and Perry explore how founders and teams can bridge the gap between marketing and sales, transform chaos into consistency, and design systems that build trust over time — not just conversions. They dig into:
Why marketing and sales silos still exist (and how to break them)
How to map your customer journey using a whiteboard, not a dashboard
Building automations that feel human — from welcome emails to onboarding flows
The psychology behind customer trust and why email still outperforms social
New frontiers in automation, including WhatsApp integration and conversational AI
How to “turn the lights on” in your marketing house — and stop losing leads you’ve already paid for
Whether you’re an entrepreneur trying to scale your first system or a marketing leader rethinking automation strategy, this episode offers a grounded, tactical approach to customer-centric growth.
Perry Sheraw is a strategist, consultant, and speaker specializing in marketing automation and customer experience frameworks. She’s led marketing and call center operations for highly regulated industries, built cross-functional CRM systems, and currently advises companies on scaling automation with empathy. Perry is also writing a forthcoming book on marketing automation frameworks for young professionals — a practical guide on integrating automation and selling it to the C-suite.
Learn more at perrysheraw.com
Show links:
• Connect with Perry on LinkedIn
• HubSpot – hubspot.com
• Mailchimp – mailchimp.com
• Klaviyo – klaviyo.com
• Seth Godin – “Permission Marketing”
• Neil Patel – neilpatel.com
High-level takeaways:
• “If you invite people to your house and then leave, that’s what it’s like sending paid traffic without follow-up.”
• “Automation isn’t about removing the human — it’s about meeting them where they are.”
• “Start your customer journey on a whiteboard, not in a platform.”
• “Marketing and sales are two halves of the same customer conversation.”
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