Transportation Workforce Investment Act of 2020 This bill directs the Department of Transportation (DOT) to establish a program to provide competitive grants to institutions of higher education, states, and other partnerships to support transportation sector education and workforce development projects. The bill expands authority for DOT to provide grants for surface transportation workforce development, training, and education to include (1) on-the-job training or work-based learning opportunities, including pre-apprenticeships and registered apprenticeships; (2) activities to support the establishment of industry or sector partnerships; (3) activities to increase the number of underrepresented individuals in such workforce; and (4) activities to update facilities and equipment used in career and technical education programs of study. DOT must also establish a task force to (1) conduct an assessment of the current and projected state of the transportation workforce, including any existing barriers to attracting, developing, training, or retaining a skilled transportation workforce; and (2) develop recommendations and strategies for DOT and states to improve the transportation workforce based on such assessment.