Safety is the number one priority for the Federal Motor Carrier Safety Administration (FMCSA) and the U.S. Department of Transportation (USDOT). While roadway fatalities declined consistently from 1972 through 2020, the progress stalled and fatalities began to increase. Vision Zero is the commitment of FMCSA, and USDOT as a whole, to zero serious injuries or fatalities on our national highways, roads, and streets. While safety is the primary driver for all technology initiatives at FMCSA, the technology enablement of safety strategy has historically presented a significant challenge due to enormous technical debt. This experience report examines the culture shift at the Office of the Chief Technology Officer (OCTO) leading digital transformation and developing sustainable products to improve interactions between regulators and regulated entities. Using the development of SafeSpect, FMCSA’s next-generation roadside inspection software that forms a key component of the safety strategy, as a case study, we demonstrate how FMCSA is effecting a radical shift in the product space of safety technology and delivering capabilities at a rapid pace. SafeSpect, as a product, breaks the traditional norm of the technology industry leading the federal government in terms of technology and innovation by providing capabilities that are unique to SafeSpect. FMCSA OCTO strives to build on the success of SafeSpect to continuously deliver safety-related technology products and capabilities that provide a sustainable complement to regulations and policy and help the organization realize Vision Zero.