Digital transformation of the marketing organization forces firms to develop new digital marketing capabilities (DMCs) to remain competitive. However, despite considerable academic and managerial interest, the value relevance of DMCs beyond the value achieved through classic marketing capabilities (CMCs) remains unclear. Similarly, research investigating the interaction effect of DMCs and CMCs is scarce. We address both research gaps by drawing on a mixed-methods approach combining in-depth interviews and a multi-industry, multisource dataset. The results reveal that DMCs significantly contribute to firm profitability beyond the influence of CMCs. Drawing on the contingent view of resource-based theory, we investigate the moderating influence of organizational and environmental contingencies on the interaction effect of DMCs and CMCs. This investigation reveals important tradeoffs that result in actionable managerial implications for realizing the complementarity potential—and preventing the substitutive potential—of a firm’s DMCs and CMCs.