Great pay and benefits, but poor leadership support
Pros
The pay and benefits are awesome. Healthcare and added corporate perks are some of the best. If you can make a strong territory you can make a lot of money.
Cons
A LOT. I have worked in tech sales for years and for competitors and I can tell you that Square is light years behind in the way that they coach, support, and in creating business systems that have real impact. Leadership changes as fast as anywhere I’ve ever been if one half or quarter goes bad. The data is so bad which is one of the reasons all the AI tools they try and slap on salesforce never have any real impact. ROE means nothing here either, it’s the Wild West and its dog eat dog. Whoever knows the right person and gets the lead first gets the deal so it can be inequitable compared to other sales orgs. Lastly the whole sales leadership team just sends pump up messages as the way they think they’re supporting the team. The lack of authentic support just makes reps miserable and makes them feel isolated. Especially because they know they’re always on the chopping block if they have a bad Q
