With the emergence of digital credentialing and platforms to support learners and workers with entering and traversing the increasingly skill-based education and workforce ecosystem, Learning and Employment Record (LER) technologies have been identified as a promising solution for individuals to share and access their learning- and skills-data and to education and career opportunities. However, learning journeys are rarely continuous; opportunities, challenges, and evolving circumstances can result in both the development of skills and competencies and a change in the way in which individuals demonstrate and get recognized for their skills and competencies. Further, systemic barriers and inequities disproportionately impact learning transitions for historically and systematically excluded (HSE) communities, barring access to supports and resources to enter and persist in the education and workforce ecosystem. To help inform the the design of LER technologies to be of value and useful in supporting HSE learners and workers during learning transitions and along multiple pathways, this report highlights the following: (1) co-design methodologies and experiences that center HSE learners and workers in LER design, development, and testing; (2) recommendations and insights from HSE learners and workers on the opportunities and challenges of utilizing LERs through education and career pathways; and (3) seven learning transition design principles that support the multiple and often fluid transitions between education and the workforce that many HSE communities experience. These findings will inform the future work in developing a certification that guides developers to center HSE learners and workers as they design LER technologies to support individuals over time and through learning transitions. Based on these findings, LER developers, postsecondary education providers, and the workforce ecosystem, may develop a more inclusive skills-based learning and employment record system.