Case Study: Pennington & Bailes achieves 53% increase in opens and 114% increase in clicks with Windsor Circle

How Pennington & Bailes leverages predictive analytics to create a Win-Back series that sees 2x the opens and 4x the clicks

Pennington & Bailes is a family‑owned apparel brand best known for its Green Pants and decade of work in collegiate and lifestyle clothing. As a small business, they faced customer churn—previously high‑value buyers falling out of purchase cycles—and needed a scalable way to win those customers back.

Working with Windsor Circle they automated two tailored 3‑email Win‑Back series: one for 1–2x purchasers (timed at 120/240/365 days) and one for 3+ purchasers triggered by a customer‑level Predicted Order Date (40/80/120 days after prediction). Emails use first‑name personalization, dynamic “Hot Combo” product recommendations and escalating discounts (15/20/25%). The campaigns now drive 50% of Pennington & Bailes’ data‑driven email revenue and have lifted overall open rates by 53% and clicks by 114% (average opens 24.5%, clicks 3.5%; 3+ purchasers reached 39% opens and 8.3% clicks with particularly strong lifts).

Pennington & Bailes

Tygh Bailes

Founder