Things are going downhill - Seller Advanced Support Specialist Square Employee Review

3.0
Apr 17, 2022
Recommend
CEO approval
Business Outlook

Pros

The health insurance/dental/vision benefits are top tier. Probably the best. Leads are easy to talk to and employee resources are easy to find when you need them, everyone is very helpful to point you in the right direction when you’re lost Paid holidays/extra pay on holidays Inclusive to lgbt+ culture, understanding of disabilities that might need accommodation Bi-annual reviews with potential for a raise or promotion Reimbursement for internet/electricity bills Completely remote 401k

Cons

0 work/life balance if you are in a customer-facing role. This job will consume your entire life. You are forced to change your schedule every 4 months - including having to work on weekends. The accrual rate for sick days is completely unreasonable. Teams that aren’t customer-facing can take pto whenever they want, and they get all the holidays off - but the rest of us have to ask at least 2 weeks in advance and there’s many days we are not allowed to ask for off. We are not guaranteed any holidays off. This job is not ideal if you have a family that you’d like to spend time with. The workload keeps getting piled higher and higher while the pay stays the same.

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5.0
Mar 4, 2026
Recommend
CEO approval
Business Outlook

Pros

Had an amazing time building with AI

Cons

got removed by artificial intelligence

2.0
Jul 13, 2026
Recommend
CEO approval
Business Outlook

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

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