-Sales team is relatively new to the business- has only been around ~2 years, so doesn't have a lot of processes or tools in place that you might expect a company as well-known as Slack to have (for example, AEs aren't provided with any sort of VOIP or calling software- have to dial from your cell).
-Competition against MS is real- long-term, I think Slack will take-off like a rocketship, but there are definitely competitive headwinds, especially with the economy down and MS giving Teams away for free
-Because Slack can truly be used for 1000s of use cases and by any line of business at a company, finding one ubiquitous value prop can be a struggle when people ask, what does it do? It's a blessing and a curse
-The culture is solid, but it does seem like sometimes it's hard to be completely honest when things suck or a process isn't working, as optimism is heavily rewarded at Slack. In general, I love an optimistic outlook, but you also want to create a safe space for employees to be brutally honest about the problems they see in their team, the product, strategic approach etc. This isn't a Slack-exclusive problem, but it does seem like if leadership led the way showing that voicing concerns and being real about when there are problems and that people should be rewarded for this kind of feedback rather than seen as "not being a team player" would go a long way.
-401 (k) match is capped at $4k right now- would be awesome to see some sort of % match and this limit increased- but the rest of the benefits are top-notch :)