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.

Here’s a glimpse of what you’ll learn:

• [1:23] Aaron Schwartz shares his career trajectory from founding Modify Watches to co-founding Orita.ai 
• [4:22] Why brands overuse email during downturns and how it hinders engagement and deliverability
• [9:20] How machine learning reveals insights missed by rules-based customer segmentation
• [15:17] Why inbox placement and timing matter more than click or spam metrics
• [19:51] Common mistakes brands make in retention marketing
• [23:18] How retention marketing leadership varies across organizations
• [31:34] The founding story of Orita.ai
• [35:42] Aaron’s views on AI and personal shopping agents

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 Shifting from a marketer’s mindset to a consumer’s perspective — and using modern analytics instead of outdated rules of thumb — can transform email, SMS, and direct mail into profitable retention channels.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.

Resources mentioned in this episode:

• Aaron Conant on LinkedIn   
• BWG Connect  
• Aaron Schwartz on LinkedIn 
• Orita.ai
• “AI’s Missing Link: How Data Readiness Unlocks AI’s Full Potential With Joe Luchs” on The Digital Deep Dive 
• Datalinx AI

Quotable Moments:

• “Let's not think about segmentation based on time bound. Let's go build a very, very big model.”
• “Take off your marketer hat and put on your consumer hat; don't be the brand that emails somebody.”
• “Stop thinking about metrics and start thinking about your customer and when they want to hear.”
• “If you're not questioning your priors all the time, those are the places it becomes hard.”
• “Focus on what is the job to be done first before you go try solutions.”

Action Steps:

1. Use data-driven segmentation instead of rules of thumb: Relying on clicks or opens over fixed timeframes misses valuable customers. Machine learning models uncover deeper engagement patterns and help send the right message at the right time.
2. Balance communication frequency with customer preference: Over-sending emails can lead to unsubscribes and deliverability issues, even if it boosts short-term revenue. Respecting audience tolerance builds long-term trust and stronger retention.
3. Expand beyond email to multiple retention channels: SMS and direct mail can be profitable when targeted to the right segments. Diversifying outreach increases touchpoints without overwhelming customers.
4. Adopt a consumer-first mindset in marketing decisions: Thinking like your customer shifts the focus from what the brand wants to when the customer is ready. This improves engagement and reduces wasted effort.
5. Align leadership expectations with data insights: Mandates to send more campaigns often conflict with what the numbers say will work best. Empowering teams to follow the data prevents burnout and strengthens customer relationships.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.