Pros
Working at Adaptive Road, every employee works remotely. While I thought this would be a major challenge, the communication is still better than at any other place I've worked in a traditional office environment. The structure of the organization is something called Holacracy, which eschews typical hierarchical management structure in favor of 'circles' (departments) and 'roles' (job descriptions). This takes some getting used to, but it is very powerful and very freeing. It focuses on the projects that are underway, the work that needs to be done, and it presupposes that employees are responsible enough to get their work done. No micro-managing here. The company offers an ESOP to all employees once they are eligible (have to work there for a certain amount of time first), which is a nice alternative to a traditional 401K or IRA. You can set one of those up too, if you want. As such, most employees are also employee-owners, which really helps to ensure that those who stick around really care about seeing the business succeed, and don't merely work the bare minimum to collect a paycheck. As it is a small team, the workload can vary, which means you may also be asked to help out in areas other than what you were hired to do, if they fit your talents and strengths. For someone who is interested in learning a lot in a variety of different disciplines, this is awesome. There are no set hours, and the compensation incentives are structured such that if you want to do more work, you have the opportunity to make more. The company (and its parent company) are really good at hiring very smart, driven, passionate people. You aren't likely to find another group of coworkers who are as intelligent and as good at what they do. Very little travel is involved (for consultants at least), but some is.
Cons
It is remote work, so think a lot about whether you are ready to work from home 100% of the time, if you don't already. Set up a separate space (preferably a different room as your 'office', if you can) to work in, so you can maintain a healthy mental work-life balance. Holacracy isn't for everybody. If you want to be told what to do / directly managed, instead of holding yourself accountable for your own projects, then you may not like it. However, if you do like it, it will ruin you in that you will probably never be satisfied by other companies if you ever leave (I assume; I haven't left). The workload for the small team ebbs and flows, so you won't have a completely full plate all of the time. If you can't find productive ways to make yourself useful otherwise (learning, helping out with presales, or helping with marketing efforts for example), you may feel frustrated. This expectation is set at the outset during interviews, so you shouldn't be surprised by it really. The ESOP doesn't kick in for a while, so you will have a gap in any employer-based contributions to a retirement plan/account. This isn't a big deal if you can just contribute to a personal IRA or something like that in the meanwhile.
