Careers in information systems and technology are top-rated and growing, yet universities are challenged to recruit students into information technology (IT) majors and organizations struggle to find talent with IT and digital skills. Experiential mentorship programs offer an opportunity for both academia and industry to attract students into university programs and ultimately into IT positions when they graduate. Therefore, to address the goal of developing digitally proficient, meaning technically and analytically strong, students and talent, this teaching tip presents a digital-ready mentorship program designed to connect technology students with industry as a part of their undergraduate education. This program has been in place since fall 2019 and has facilitated a total of 50 students in five cohorts. As a part of this work, we present the digital-ready mentorship program, teaching approach, lessons learned, and evidence from the project outcomes and learning experience. We hope sharing this program will inspire other universities to develop similar programs with industry partners and ultimately address the IT labor shortage.