Square reviews

3.7

63% would recommend to a friend

(22 total reviews)

Jack Dorsey

52% approve of CEO

41% positive business outlook

Reviews by job title

22 reviews

Reviews about "Compensation"

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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

1.0
May 14, 2025

10/10 would NOT recommend

Recommend
CEO approval
Business Outlook

Pros

the people are great! I cannot lie about that - but it's most likely because we are constantly trauma bonding over the new updates from SQ.

Cons

Jack is a mess. no internal movement. poor compensation. constant layoffs. middle management is useless. Jack is replacing everything with AI, no one is safe. lack of transparency. leaders are afraid of change and still think its 2011, causing issues within the company / causing it to remain at a standstill. the product itself needs improvements, we hear it all the time from customers who are churning - yet no product improvements have been made.

4.0
Feb 5, 2025
Recommend
CEO approval
Business Outlook

Pros

-Benefits are fantastic. The healthcare is the best I've ever had and they offer free dental and vision insurance. Good 401k matching and stock options available. -The community groups are wonderful. Parents, Pride, Women Engineers, Afroblock, etc. They offer opportunities to connect and get support from others across the company. -In-person meetups are great (when they happen). -Company provided laptops and work from home stipend with the option to work in-office if location permits it. -There are so many truly talented, smart people working there who I learned a lot from in my time at Square.

Cons

-Lack of empathy from Jack and upper management especially after repeated layoffs. The message was basically "deal with it or leave" after laying off over 1000 employees and moving their workload to others. -Jack's "inner circle" is a group of cherry-picked yes-men with no transparency. They are the real decision makers at Square. -While Square preaches equality and diversity, there is still a lack of accountability when incidents occur. I've witnessed discriminatory and misogynistic leadership succeed while "problem" employees are quietly pushed out. -Benefits are slowly being stripped away, ie. bereavement leave which was reduced to just a few days for the death of a close family member including a child or spouse. -Customer service reps are treated as dispensable and jobs are being farmed out to other countries so Square can pay less per employee. The quality of customer service has gone down significantly because of this. -Your experience is very dependent on which team in which department you are in. Some are better than others and consistency between orgs is lacking. -Stack ranking for raises is deeply problematic. I've watched high-performers get no raise and a poor rating so that others could get promotions because they are severely limited by upper management. So much is dependent on your managers opinion and oftentimes how much they like you. Bias is a huge problem.

Viewing 1 - 3 of 22 Reviews

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