Unified billings

When Workleap became a platform of six products, billing quickly emerged as a blocker for growth. Each product had its own way of charging customers: some billed by seats, others by groups, templates, or documents. For admins and decision-makers, understanding invoices across products was confusing and error-prone.

The initiative had two main goals: to make billing fully self-serve so customers no longer needed to go through sales or support for routine tasks, and to create a unified system that would unlock cross-sell and bundling opportunities. Strategically, billing wasn’t seen as a direct value driver, but it was an essential enabler for Workleap’s platform ambitions. A smoother, more consistent experience meant higher adoption and more natural upsell paths.

I worked closely with product managers and engineering to rationalize the different billing models. We decided to adopt the system that was already the most widely used at Workleap and flexible enough to cover our needs. This choice reduced the learning curve internally and gave us a strong baseline for unification.

There were difficult tradeoffs along the way. In the first release, for instance, we couldn’t deliver a single consolidated receipt. Instead, I designed a stopgap where admins could download all receipts at once in a zip file. Although the experience was not ideal, it still solved the most painful part of the process and was well-received by customers.

On the technical side, the billing tool we relied on had significant limitations. To overcome them, I pushed for building additional mechanisms on our side of the platform, ensuring we could deliver the experience we envisioned. This required tight collaboration with engineering to explore options and deliver value in the leanest way possible.

The result was a unified billing interface where admins could manage all subscriptions in one place, clearly understand the number of seats per product, and take advantage of discounts when purchasing multiple products. We also designed ways for admins to explore related products directly within billing, using small contextual banners that highlighted synergies between tools. For example, an admin managing engagement with Officevibe would naturally see how their workflow could be extended with onboarding or performance management.

Behind the scenes, we built custom logic that recognized when a customer already owned multiple products and automatically triggered discounts. What used to be handled manually by sales now happened seamlessly within the product.

The impact of the new experience was immediate. Self-serve transactions increased by 15 percent, freeing the sales team to focus on larger accounts. Cross-sell and bundling also grew by 10 percent, showing that the billing experience had become an effective driver of product adoption. Internally, the move to a single billing management tool saved time and simplified operations.

For me, the most important learning was that simplicity at the platform level requires absorbing complexity on the company’s side. Before, customers had to carry that burden every time they wanted to buy a second product or adjust their seats. By taking on that complexity ourselves, we created an experience that felt effortless and cohesive for admins.