Aaron Schwartz is the Co-founder and Co-CEO of Orita.ai, a software company that improves email deliverability. He is also an advisor and investor in various commerce tech companies, including Passport and EcoCart. Previously, Aaron built and managed the DTC brand Modify Watches and was the President of Loop.

In this episode…

Email remains a core channel for reaching customers, but brands often misuse it. As customer acquisition costs climb and competition intensifies, many brands resort to blasting their audiences with more campaigns, only to see engagement fall and customers unsubscribe. How can companies harness smarter strategies to keep customers engaged without burning them out?

According to eCommerce veteran Aaron Schwartz, the answer lies in data-driven retention marketing. Over-sending emails may provide a short-term lift, but ultimately damages deliverability and customer trust. By tapping into customer behavior data, brands can determine when someone actually wants to hear from them, creating more meaningful engagement. Shifting from a marketer's mindset to a consumer's perspective — and using modern analytics instead of outdated rules of thumb — can transform email, SMS, and direct mail into profitable retention channels.

In this episode of The Digital Deep Dive, Aaron Conant talks with Aaron Schwartz, Co-founder and Co-CEO of Orita.ai, about retention marketing best practices. Aaron discusses why brands must move past intuition and embrace data, how machine learning enables smarter segmentation, and why balancing timing with customer preferences drives higher ROI.