Pros
The benefits package is truly exceptional, especially for a startup of this size. Earlier I worked for an established, profitable company with solid benefits, and I was amazed at what Human Interest offers. They offer WFH cash support, paid equipment, wellness cash support, and---when I joined at at least---they paid cash directly into your FSA/HSA. They also have unlimited PTO, which you are encouraged to use and people respect. There is solid leadership in the Tech organization, not just at the very top, but also in several levels within. The company has some strong external tailwinds and has developed solid moats against competition. There is a huge TAM (total addressable market), and the industry is resilient against economic problems. All it really depends on is employment and small-to-midsize companies---and the US has demonstrated exceptional economic endurance even during recessions (even in 2008-2011, unemployment barely scratched above 10% compared to much, much higher rates in Europe). If you are a sales person, I think it is likely a pretty positive environment. It's pretty easy to earn bonus commissions, and the product is pretty easy to sell.
Cons
The company has a very mixed culture because there are broad divergences in customer focus among stakeholders. Some people in the org really care about the customer and trying to serve them with a plan that meets their needs. Others are just looking to sell whatever plan will make the most money for themselves or the company, even if it is not what the customer needs or wants. With some exceptions, the top leadership is extremely weak; this is a real issue because the company is at a point where it needs to transition away from 100% revenue growth and become more of a "real" company who cares about things like cash flow, margin, CAC, and LTV. Regrettably, the current leadership [again with some exceptions] are more suitable to early-stage start ups whose focus is on investor buy-in, funding, and revenue growth rather than company fundamentals. Before giving some examples, I should mention that there have been some recent signs of hope. About a year ago they hired a CTO who is definitely a step in the right direction, and more recently they brought in a new Finance VP who recognizes the importance of indexing on LTV and net income rather than other metrics. The weakness in Leadership has had many negative consequences: -- The whole company is currently effectively structured to maximize revenue because that is what Leadership has historically cared about. This means that salespeople are incentivized purely on anticipated revenue rather than actual cash flow, margins, LTV, etc. This leads to deals that have horrible margins---some even being negative LTV. It also means that CAC is out of control. If you incentivize revenue, don't be surprised when margins are poor. -- Leadership has a history of focusing on metrics that make the company look good rather than metrics that actually improve the company's fundamentals. The outcome of this is that people are hired to improve some metric that we may not be in a position to improve and---even if we do improve it---will not lead to material improvement for the business. -- Because of the above, Leadership has shown no interest in understanding the company's actual business model. They care about revenue, so the finance team built a model to estimate revenue for various deals, but there was no interest in really understanding costs, margins, or LTV---the idea that we should know/project these metrics at the deal level to know which deals are good and which deals are bad seemed to never occur to Leadership. This means that leadership simply does not understand the actual business because they did not invest in gaining understanding of what influences these core metrics. -- The focus on Revenue causes Leadership to focus on "easy solutions" that are unreliable rather than considering tradeoffs between Revenue and margins. Because their understanding of the business model is weak, these easy solutions can backfire. To give an example: for the last 12-15 months there has been a steady notion that "if we just get more clients to do X and Y, all of our problems will be solved." And lots of $$ and energy was spent trying do X and Y, with lots of bad deals made to accomplish X and Y.... and it turns out that X is actually bad for business! So millions of dollars have been spent on initiatives that actually lead to worse outcomes for the company. Had leadership invested more in really understanding their business model, this could have been avoided. Another example: the company wanted to improve Gross Margin. We have levers we can use to accomplish this: we can reduce our discounting, we can sell fewer BPO plans, we can stop waiving setup fees, we can pursue customers that we know historically lead to higher margins. But instead of using these means (many of which would trade off Revenue for better margins), the company just did a round of lay-offs to reduce costs. And then, after letting so many people go, they did not have sufficient staff to handle some major deals that came in later.