Pros
Lighter Capital has an entirely remote workforce, but tries hard to build and maintain a team atmosphere through frequent remote interactions and twice-yearly retreats. The management team values open communication and shares challenges as well as successes. The culture focuses on making our portfolio companies successful, and that culture of helpfulness permeates the organization - e.g. Engineering is highly responsive to the needs of Sales, etc. This leads to a very positive atmosphere, as helping others (internally or externally) is celebrated and rewarded. That both selects for co-workers that are friendly and helpful, and encourages everyone to be more so.
Cons
Lighter Capital is, despite being 12 years old, still a start-up in many ways, so doesn't have the formal structure or resources of a larger organization. For example, HR is spread across several people, some of whom are part-time, and all of whom have other responsibilities. This means that there isn't always an obvious person to go to about things like health insurance questions, and the people who can help have a lot of other things going on. Everyone tries to be helpful, but there definitely isn't anyone sitting around waiting to address an issue with a reimbursement or whatever.