The effects of the EU measures and the financial crisis limited the potential growth of the Italian small medium enterprises (in term of loss of productivity, increase of unemployment rate, and decrease of customers purchase power). Together with these two factors, the Italian economic system competitiveness (whose backbone is represented by the SMEs) was negatively affected by the “digital disruption.” The purpose of this article is to critically analyse the main causes of this competitiveness loss for Italian SMEs and the role of strategy consultants in helping them to improve their results and their presence in local and international markets. Leveraging on their past industry/service line experience and massive investment in digital transformation (e.g., acquisitions of IT companies, alliances, specialization in software/tools, and internal reorganization), strategy consultants are able to assess, suggest, and implement their clients' digital strategy.