Small businesses are being encouraged to use digital technologies more than ever before. However, the greater emphasis on technology adoption puts underserved minority business owners (those who traditionally have faced barriers in accessing credit, capital and other resources) at greater risk of being left behind. We take an assets-based approach to understand business owners' strengths and challenges in adopting and using digital technologies. We then implement a community-based intervention---Community Tech Workers (CTWs)---to bridge the growing socio-technical gap in the context of small businesses on Detroit's Eastside, which are primarily Black-women-owned businesses. We take a mixed-methods approach, using a combination of a survey, interviews, and observations, to outline how the CTW program 1) helps businesses determine where to start with technology use, 2) offers support grounded in the day-to-day realities of running a business, and 3) builds caring relationships with business owners to foster trust in technology support services. We suggest opportunities for a more collective perspective on assets-based community development and outline considerations for building culturally-conscious ecosystems of support for digital engagement.