Vantaggi
I've been through an acquisition as well as an IPO and Iterable has all the pieces it needs to succeed: a strong leadership team, an amazing culture, people doing their best work across the entire org, a leading product in its space, high customer retention, a killer sales team, and a fantastic brand identity. If you have an opportunity to join, I would not turn it down.
Svantaggi
There's a lot of work to be done, but if you're attracted to startups this shouldn't really be a con. You most likely want to make an impact and you'll definitely be able to do that here.