Jennifer Dennard, the co-founder of Range Labs, shares insights on the challenges and adjustments faced during the transition to remote work. In the conversation, she reflects on her personal experience, noting that being childless made the shift relatively smooth for her. Having previously engaged in some remote work, Jennifer emphasizes the importance of setting up a dedicated office space, revealing that she works from a compact three by six closet in her San Francisco apartment. However, she acknowledges the struggle for colleagues with children, highlighting the necessity of adapting to their varied schedules. The discussion delves into the concept of “windowed work,” recognizing the need to adapt working styles to accommodate different time availabilities. Jennifer explores the nuances of breaking down the workday into distinct moments, such as collaboration, focused work, and social connection, emphasizing the challenge of replicating organic interactions that occur in a physical office space. She discusses the intentional efforts made by her team to architect routines that foster productivity and cohesion, drawing on their extensive experience with remote work. Despite the stabilizing effect over time, Jennifer acknowledges growing pains and occasional hiccups, citing instances where team members needed to address interpersonal issues through impromptu calls. In conclusion, she recognizes the ongoing difficulty of the remote work transition for various team members based on their individual circumstances, emphasizing the importance of adaptability and intentional structuring of remote work routines.