Solving A 10-Year Business Problem In Two Weeks
How questioning a single assumption unlocked a business problem that had existed for over a decade.
Some business problems survive for years not because they are difficult, but because everyone eventually accepts them as part of reality.
This was one of those problems.
The Situation
The organization had been selling subscriptions successfully for years. Customers could purchase products, revenue continued to grow and the overall business was performing well. Yet one metric consistently attracted attention: a significant number of customers abandoned the purchase process shortly before completing checkout.
The reason was well understood. Throughout the customer journey, products were presented with a monthly price. However, during checkout, customers were asked to pay for an entire year upfront.
From a business perspective, the model made perfect sense. From a customer's perspective, it often felt like a different offer than the one they had been evaluating moments earlier.
The Assumption
What made the problem interesting was that it was not hidden. Everyone knew it existed. The organization had been aware of it for years.
The real assumption was that solving it would require changes that were too expensive, too risky or simply impossible within the existing systems and processes. As a result, discussions focused on optimization rather than elimination.
Teams analyzed conversion funnels, reviewed user journeys and explored improvements to the checkout experience. Various initiatives were proposed, but none fundamentally changed the outcome.
The problem was known. The assumption was that it could not be solved.
The Question
When we started examining the situation, the most interesting question was not how to improve the checkout process.
The more interesting question was whether annual upfront payment was truly the only viable business model.
That single assumption had remained largely unchallenged for more than a decade.
The Solution
Instead of redesigning the checkout flow yet again, we explored a different approach. Customers could register a payment method once and continue paying monthly, creating an experience aligned with the pricing they had seen from the beginning of their journey.
Suddenly the conversation changed. We were no longer discussing buttons, forms and screens. We were discussing customer expectations, trust and business outcomes.
The Result
What initially appeared to be a technology problem turned out to be a business problem. What looked like a checkout problem was ultimately a pricing and customer expectation problem.
More importantly, a challenge that had existed for more than ten years became solvable once the right assumption was questioned.
The quality of the solution is often determined by the quality of the question.
What I Learned
Throughout my career, I have seen organizations spend enormous amounts of time and money improving solutions that were built on top of incorrect assumptions.
The fastest way to solve a ten-year problem is not always better technology. Sometimes it is simply the willingness to challenge something that everyone else has accepted as obvious.