When a company is growing as quickly as Smartsheet is, it can be difficult to ensure they systems and processes are scaling quickly enough to properly support that growth. This is to be expected in this type of environment but when you run into these issues, it can be painful. The company and the leadership team are quick to try and resolve the issues but it can be frustrating for sales people who have come from more mature selling environments where these problems may already have been addressed and they haven't had to live through them.
Unforeseen (or maybe foreseen but not prioritized) challenges are a reality of this type of growth and while I list these as cons, it would be unrealistic to expect there to be none. When considering what Smartsheet is trying to do from a growth perspective, these can be easily overlooked.
Lastly, because the product serves so many markets and potential buyers, there is no clear playbook on how to be successful. Most companies usually have an offering that solves a very specific problem, for a specific audience, and offers a specific value prop. For Smartsheet, all of those elements can vary wildly between customer engagements. While that makes the selling environment mentally stimulating, it also makes it harder than in other companies. Smart, curious, creative, and hardworking people will thrive here. People looking for an easy place to land will be miserable and I would encourage them to continue looking elsewhere.
