Transitioning between different types of professional roles can be challenging — new expectations arise, and fresh ways of seeing the world are required to be successful. A few weeks ago, I interviewed Anjul Bhambhri of Adobe about how she transitioned from engineering into product, where she now leads the company’s customer experience cloud.

This week, I chatted with Toby Russell, the co-CEO of online used car marketplace Shift, which generated $135 million in revenue last year and has raised $293 million in venture capital according to Crunchbase. The company is targeting an IPO in 2021.

While we have written a lot about Shift, we have written far less about Russell, whose career spans a model he calls “learn, earn, and serve.” He received a PhD in international relations at Oxford, switched to founding a startup, then served in the Obama Energy Department, before heading over to Capital One to lead digital and eventually rejoining his friend George Arison and Shift’s co-founder as co-CEO.

Across these roles, Russell has had to adapt to very different environments, and we chatted about those transitions, his lessons learned, and his approach to leadership.