In complex systems, small decisions compound. For RRx, a pharmacy rewards program within CVS’s ExtraCare ecosystem, a single change in language and flow triggered a 1000% increase in enrollments — and revealed how clarity, context, and customer behavior can transform both customer experience and organizational alignment.

This case study chronicles the evolution of a startup navigating the complexities of scaling and implementing system-wide changes. It highlights the challenges faced, strategies employed, and the insights gained during the transition from a nimble startup to a more structured organization.

Tech debt isn’t just code or engineering overhead — it’s a business strategy issue. When framed in business terms, paying down tech debt shifts from being an internal burden to becoming a source of revenue growth, efficiency, and innovation.