Traditional models of academic leadership are based largely on managerial and transactional approaches. Such efforts frequently support status quo individual success rather than values-based leadership based on collective institutional or sustainability-centered pursuits. Evolved reward systems and leaderships modes that support collective and institution-level effort and innovations prioritizing community and sustainability require new leadership models. Innovative leadership models that transcend traditional gatekeeping are needed and four leadership modes to support innovation and collective efforts are discussed, including shared leadership that draws on distributed contributions of multiple individuals; creative or innovative leadership that requires risk-taking, experimentation, and experiential learning; qualitative leadership that is data-driven and includes evidence-based innovation; and, dynamic leadership based on demonstrated agility and ability to traverse different spaces using diverse modes of doing and thinking. Progressive leaders can move in and out of these modes in response to ecosystem needs, demands, and changes through the use of design thinking and initiatives to support innovation and sustainability in higher education. Success in evolved leadership approaches, including centering sustainability goals that impact institutions themselves and communities in which they exist, require aligning reformed leadership goals and practices with funding models and reward systems, as well as policies and institutional change strategies.