Building a VIP Community That Drives Retention With Jenna Habayeb

In this episode of Earned, CreatorIQ CMO Brit Starr sits down with Jenna Habayeb, President of Posh Peanut and four-time CMO (formerly of IPSY and Ruggable), to unpack how community, speed, and product obsession power sustainable brand growth. Jenna shares Posh Peanut's origin story—founded by Fiona on Etsy—and how the brand differentiated itself in kids apparel through buttery-soft viscose bamboo fabric, bold maximalist designs, and a founder-led commitment to listening closely to customers. At the center of the conversation is retention. Jenna explains how Posh Peanut's exceptional repeat purchase rates are fueled by both product quality and a highly engaged VIP Facebook community of nearly 250,000 members. This community plays an active role in shaping the business—providing real-time feedback, influencing product decisions, and getting early access to launches. Brit and Jenna dive into Posh Peanut's fast-paced drop model, from weekly collections to daily drops during key moments like Black Friday and "Poshmas," and how scarcity and newness keep customers coming back. Jenna also reflects on her transition from CMO to President, why brand and performance must work together, and how creators drive a full-funnel flywheel—from ambassador content to paid amplification and organic celebrity momentum. Looking ahead, Jenna shares the key questions brands should be asking as they scale: balancing acquisition and retention, evolving distribution, and defining the right role for AI in the business.

In this episode, you'll learn:

1. How community engagement fuels retention and product demand.

2. The importance of hands-on founders in sustaining momentum and trust as brands scale.

3. Why weekly drops and creator moments keep customers coming back.

Connect with the Guest:

• Jenna's LinkedIn - @jennahabayeb

Connect with Brit Starr & CreatorIQ:

• Brit's LinkedIn - @britmccorquodale

• CreatorIQ LinkedIn - @creatoriq

Follow us on social:

• CreatorIQ YouTube - @CreatorIQOfficial

• CreatorIQ Instagram - @creatoriq

• CreatorIQ TikTok - @creator.iq

• CreatorIQ Twitter - @CreatorIQ