This study presents the first large-scale analysis of the role of unions in how technological change impacts transitions to new employment following job loss. The authors use large-scale matched employer–employee data from the Netherlands for the period 2001–2016 to assess how technology implementation within enterprises impacts the job search duration among workers whose job ended during the implementation period. The authors study to what degree industry unionization moderates this impact. They find job searches to be significantly longer in enterprises implementing new technologies, but industries with stronger unions exhibit a weaker association between technology implementation and job search duration. The results suggest unions enhance training, and re-education, and facilitate work-to-work transitions, increasing the employability of workers under technological change.