Problem

As a new sportsbook preparing to launch, Underdog needed a bet placement experience that could handle complex betting logic and strict compliance without overwhelming customers. Because bet placement is the highest-leverage moment in the product, any confusion or errors directly impacted conversion and revenue.

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The challenge

We needed to design a checkout that reduced cognitive load while still surfacing legally required information and handling frequent errors like odds changes and invalid selections. The experience had to feel fast and trustworthy at launch, without relying on established patterns or prior customer behavior.

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Decision 1: Treat cognitive load as the primary conversion risk

In a compliance-heavy checkout, the core risk was not missing information but presenting too much at once. I designed the experience to visually de-emphasize required details through hierarchy and grouping, rather than attempting to remove them. This allowed customers to focus on the bet they were placing without feeling overwhelmed, while still meeting all regulatory requirements.

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Decision 2: Use progressive disclosure to sequence commitment

Instead of asking customers to evaluate every aspect of a bet at once, I sequenced decisions so intent was established before secondary details were introduced. This reduced hesitation at the moment of commitment and kept the flow moving forward without hiding important information. The goal was not speed for its own sake, but clearer momentum toward placing a bet.

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Decision 3: Optimize for error recovery, not just happy-path speed

In sportsbook checkout, errors like odds changes and invalid selections are inevitable and directly impact conversion. I designed error states to clearly explain what changed and how to recover without forcing a restart, prioritizing trust and forward progress over raw speed.

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Outcome

The checkout launched with a 70.3% conversion rate and a 3.3-minute time to bet, improving to 75.7% conversion and 2.5 minutes as usage stabilized. Drop-off when errors were shown decreased from 41.9% to 40.6%, validating error recovery as a core conversion lever.

This work reinforced my belief that in high-stakes flows, conversion is driven less by speed and more by clarity, sequencing, and recovery when things go wrong.