How Whereby Is Navigating AI Pricing Without Breaking Customer Trust

Whereby's original billing system was built in-house with basic integrations to its payments provider. It worked — until it didn't. As the business grew, the system couldn't keep pace. Pricing and packaging changes required engineering time the team couldn't spare, and manual workarounds became the default.

Revenue recognition was its own problem. Data lived across multiple disconnected systems, and pulling it together meant hours of manual reconciliation in Excel every month. "Our revenue data was spread across multiple systems that were not communicating," says Malika Kenzhebaeva, CFO & Finance Leader at Whereby. "It was also tough to track data accurately over time and verify the accuracy of our recognized and deferred revenue."

Malika recognized that Whereby needed its billing and revenue recognition infrastructure under one system and reached out to Chargebee. The implementation covered subscription management, billing practices, taxation requirements, and payment collection across all of Whereby's markets.

Pricing and packaging flexibility: Chargebee's structured product catalog made it straightforward to experiment with pricing, iterate on sign-up flows, and launch changes quickly, without routing every update through engineering.

A single source of truth: Chargebee is now used across Customer Success for subscription and renewal management, Marketing for promotional campaigns, and Product for pricing experiments, giving every team access to the same data.

Hybrid billing motions: PLG onboarding and renewals run automatically at a global scale, while enterprise billing is handled through sales-assisted workflows with customized plans, discounts, and tax calculations. "Through Chargebee's support, we've achieved significant improvements in streamlining our sales and billing processes, enabling us to devote more time to strategic initiatives," says Tomi Oludemi, Head of Finance.

Streamlined revenue recognition: Chargebee RevRec combines billing data with Whereby's other financial data sources into a unified sub-ledger, with revenue drilldown by plan and transaction-level tax details, eliminating the manual reconciliation that previously consumed the finance team every month.

The impact has reached well beyond the finance team.

An end-to-end revenue management system

Consolidating billing, payments, revenue recognition, and reporting under one system gave the Whereby finance team something it hadn't had before: a complete, accurate picture of the business in one place. Month-end closes that previously required manual reconciliation across multiple systems now run faster and with significantly less risk of error. Automating revenue recognition processes has also reduced the compliance burden and eliminated the spreadsheet work that consumed the team every month.

Billing ownership moved out of finance and across the organization

Before Chargebee Growth (Retention), understanding why subscribers canceled required an engineer to build custom data infrastructure. That meant competing priorities, long lead times, and insights that never reached the teams who could act on them. Marketing couldn't self-serve. Finance held the data. Everyone else waited.

"A lot of those things used to sit very deep in our business intelligence tools — we'd have to go to our data analyst to get a piece of data out," says Tomi, "Whereas now it's all in a user-friendly platform. People from our marketing team can go into Retention and see how many people are leaving and why. An engineer helped us implement it within a week."

Churn data that previously required analyst support is now self-serve across finance, marketing, and customer success. Billing stopped being one function's problem and became the whole commercial team's tool.

Overage pricing that was discouraging growth has been rebuilt to reward it

Whereby's embedded API product uses a hybrid model: a base fee plus usage-based overages. As the team dug into customer behavior, they found a structural problem. Customers had no incentive to grow beyond their package because the overage rate penalized them for doing so.

"We were finding that our customers were disincentivized from getting bigger," says Tomi. "We want them to use their packages faster, we want them to grow, but they had no incentive to do that because it means they're going to be charged more at a higher rate."

Without flexible billing infrastructure, fixing that would have meant reverting to manual invoicing every time the team tested a new overage structure. With Chargebee, Whereby rebuilt its overage model to maintain customer discounts even when usage exceeds the current package, removing the penalty without abandoning the base-fee structure. The pricing change was made in the system, not around it.

Whereby is currently building the business case to implement Chargebee's usage-based billing infrastructure alongside CPQ. The driver is the same as the overage fix — the team needs to experiment with pricing structures directly in the system, not work around it.

"Right now we're limited to how we can bill and think about monetization of AI by our billing infrastructure," Tomi says. "But if we set up this usage-based billing infrastructure, the way that we can experiment and things we can do is almost limitless."

The specific challenge they're navigating is that Whereby serves both B2B customers, who track usage closely and expect transparency on costs, and consumers, who expect a predictable price and will lose trust if it changes without warning. Getting AI pricing right means solving for both simultaneously. The infrastructure has to be flexible enough to experiment, but controlled enough that no customer is surprised.