The Watch Society – Optimizing Recurring Discounts with Upsell Customization

The primary challenge was the inability to configure recurring discounts using their existing WP-Upsell plugin. This limitation directly impacted conversion opportunities and disrupted the brand’s subscription flow. Additionally, the client wanted to implement a custom-designed pop-up to guide and upsell users during their browsing or checkout journey.

The core requirements included:

  • Customizing the Upsell plugin to support recurring discounts.
  • Integrating visually aligned, responsive pop-ups as per Figma designs.
  • Ensuring compatibility with Stripe for smooth subscription handling.
  • Maintaining performance and stability on WordPress.com hosting.

Targeting a youth-centric audience, The Watch Society needed a lightweight yet scalable solution that would improve retention and boost recurring sales, without disrupting the existing store structure. AddWeb Solution stepped in to resolve these gaps through focused plugin customization and front-end improvements.

To support The Watch Society in offering a seamless and dynamic shopping experience, we focused on customizing their existing WooCommerce environment, specifically by extending the functionality of the Upsell plugin. With a strong emphasis on subscription and membership-based sales, our goal was to resolve limitations in applying recurring discounts while preserving the site’s design and user experience.

We kicked off the engagement with a detailed review of the WP-Upsell plugin’s capabilities and identified that it lacked native support for recurring discount logic. Our developers built a custom layer over the plugin, enabling it to handle dynamic discount conditions tied to subscription purchases.

In parallel, we integrated client-provided pop-up designs, enhancing upsell visibility without disrupting the shopping flow. These were designed in Figma for both desktop and mobile versions, ensuring brand consistency across platforms.

Throughout the implementation, we maintained full compatibility with Stripe for seamless billing and ensured the site remained responsive across devices. While the upsell roadmap has been temporarily placed on hold, the customized system is now primed to support future growth and advanced marketing strategies. This solution-oriented approach gave a technically sound, conversion-friendly upgrade aligned with their subscription-based revenue model.

4+

Team Members

21+

Man Days

12+

Client Calls

26+

New Features Added

We executed a precise customization of The Watch Society’s WooCommerce environment to overcome limitations in recurring discount functionalities and improve user interaction through enhanced design.

Our primary deliverables included:

  1. Custom Upsell Plugin Enhancement
    We customized the existing WP-Upsell plugin to support recurring discount logic, aligning with the brand’s subscription and membership-based revenue model.
  2. Pop-Up Design Integration
    The client-provided Figma designs for both desktop and mobile were seamlessly implemented, adding an engaging layer of interactivity to the shopping experience.
  3. WooCommerce Compatibility & Stability
    Ensured the customizations worked flawlessly with WooCommerce and Stripe for secure, recurring transactions without disrupting the checkout flow.
  4. Membership-Focused Checkout Flow
    While not a full revamp, we optimized plugin behaviors to cater specifically to subscription users, paving the way for future upsell/cross-sell strategies.
  1. Hosting & Performance Configuration
    Tested and refined the solution within the WordPress.com hosting environment to maintain optimal performance across staging and production.

This solution empowers The Watch Society to offer a more flexible shopping model, supporting both one-time buyers and members, while setting a technical foundation for future upsell enhancements.

Admin users can now configure recurring discount rules without touching code, thanks to a simplified back-end enhancement built into the customized plugin.

Mobile-Responsive

The integrated pop-up designs were fully optimized for mobile and desktop views, ensuring a consistent and appealing experience across devices.

Throughout development, we ensured compatibility between the upsell customizations and the site’s broader plugin ecosystem to avoid functional conflicts.

Though upsell and cross-sell expansions are currently on hold, the architecture allows future marketing add-ons without requiring a rework of the core system.

“ Working with AddWeb Solution was a smooth and satisfying experience. We needed specific customization within the Upsell plugin to accommodate our subscription-based business model, and the team delivered exactly what we envisioned. They didn’t just modify the plugin—they made it work seamlessly with our pop-up design and checkout flow. The team was responsive, technically sound, and made sure the solution aligned with our brand’s functionality and goals. The result improved our customer experience significantly. Looking forward to more collaborations ahead. ”

The Watch Society platform received a focused technical upgrade to better serve its growing community of watch enthusiasts. Built on WordPress and WooCommerce and hosted on WordPress.com, the site maintained its original structure while undergoing essential backend customizations.

AddWeb customized the Upsell plugin to introduce recurring discounts, a critical feature supporting the brand’s subscription and membership model. Additionally, our team integrated tailored pop-up designs for both desktop and mobile, improving upsell opportunities and user engagement.

These enhancements led to a smoother shopping experience, with improved discount logic, better checkout flow, and stronger visual consistency across devices. The site is now positioned to scale further, offering a more refined journey to its youthful target audience.

100%

Plugin Customization Achieved

40%

Faster Discount Application Workflow

100%

Seamless Pop-up Integration

25%

Decrease in Checkout Drop-offs